ࡱ> :#% !"zutPvBzK L M N O P Q R S T lmnopqrstukfM rbjbj== ".WW#\l<<<P:@:@:@8r@tAPxRB____```CEEEEEE$ Hi<`````i[__2[[[`98_<_C[`C[[$<_B @ɒ^P;:@a^dH0x2"2[PP Supporting Information for Efficient Syntheses of Novel C2-Alkylated ()-K252a Analogs Kazuhiko Tamaki, J. Brad Shotwell, Ryan D. White, Ioana Drutu, Dejah T. Petsch, Thao V. Nheu, Hong He, Yumiko Hirokawa, Hiroshi Maruta*,, and John L. Wood*, Sterling Chemistry Laboratory, Yale University, New Haven, CT 06520, USA. Ludwig Institute for Cancer Research, Parkville/Melbourne, Australia 3050 _____________________________________________________________________ Material and Methods Unless otherwise stated, reactions were performed under a nitrogen atmosphere using freshly distilled solvents. Tetrahydrofuran (THF) was distilled from sodium/benzophenone. Methylene chloride (CH2Cl2), and benzene were distilled from calcium hydride. All other commercially obtained reagents were used as received. All reactions were magnetically stirred and monitored by thin-layer chromatography (TLC) using E. Merck silica gel 60 F254 pre-coated plates (0.25-mm). Column or flash chromatography was performed with the indicated solvents using silica gel (particle size 0.032-0.063 nm) purchased from Bodman. Preparative TLC was was performed with the indicated solvents using E. Merck silica gel 60 F254 pre-coated plates (0.25-mm). 1H and 13C NMR spectra were recorded on Bruker Avance DPX-500 or Bruker Advance DPX-400 spectrometers. Chemical shifts are reported relative to internal chloroform (1H, ( 7.27 ppm, 13C, ( 77.0 ppm), acetone (1H, ( 2.04 ppm, 13C, ( 206.0 ppm), or dimethyl sulfoxide (1H, ( 2.49 ppm, 13C, ( 39.5 ppm). Melting points were obtained on a Gallenkamp variable temperature melting point apparatus and are uncorrected. Infrared spectra were recorded on a Midac M-1200 FTIR. High resolution mass spectra were acquired at The University of Illinois Mass Spectrometry Center. _____________________________________________________________________ Preparation of ketone 6.  EMBED ChemDraw.Document.4.5  A stirred solution of methyl 2-diazo-3-oxobutanoate 3 (9.50 g, 63.1 mmol), allyl alcohol ()-4 (3.00g, 63.1 mmol), and Rh2(OAc)4 (95mg, 0.44 mmol) in benzene 300 mL was immersed into a preheated (100-110 C) oil bath. The mixture was heated at reflux for 45 min, cooled to room temperature, treated with BF3OEt2 (9.60 ml, 75.8 mmol), and stirred for 3.5 h at 25C. The reaction mixture was washed with H2O (300 mL), and the aqueous layer was extracted with EtOAc (2 x 100 mL). The combined organic layers were washed with H2O (150 mL), brine (150 mL), dried over Na2SO4, and evaporated to a residue. Purification by flash chromatography (4:1 hexanes/EtOAc eluent) afforded alcohol 6 (7.61 g, 38% yield) as a colorless oil: IR (thin film/NaCl) 3485 (m), 3030 (w), 2953 (s), 2923 (s), 2857 (s), 1724 (s), 1604 (w), 1586 (w), 1453 (m), 1437 (m), 1364 (m) cm-1; 1H NMR (400 MHz, CDCl3) ( 7.39-7.25 (m, 5H), 5.55 (dq, J=15.1, 6.4 Hz, 1H), 5.26 (ddd, J=1.5, 9.6, 15.1 Hz, 1H), 4.51 (d, J=11.9 Hz, 1H), 4.42 (d, J=11.9 Hz, 1H), 4.25 (s, 1H), 3.74 (s, 3H), 3.44 (ddd, J=4.0, 5.5, 9.4 Hz, 1H), 3.36 (dt, J=9.4 Hz, 5.1H), 3.22 (m, 1H), 2.39 (s, 3H), 1.63 (dd, J=1.5, 6.4 Hz, 3H), 1.55 (m, 1H), 1.43 (m, 1H); 13C NMR (100 MHz, CDCl3) ( 205.5, 170.4, 138.4, 130.1, 128.2, 127.6, 127.5, 127.4, 88.1, 72.8, 67.2, 53.1, 45.5, 28.9, 25.5, 18.0; HRMS (FAB) m/z 320.1614 [calc'd for C18H24O5 (M) 320.1624]. ________________________________________________________________ Preparation of benzyl ether 8. EMBED ChemDraw.Document.4.5 A solution of alcohol 6 (6.50 g, 20.3 mmol) and trace of Sudan red 7B dye in MeOH (125 mL) was cooled to -78 C and treated with O3 until the dye was completely discolored (about 7 min). The mixture was purged with nitrogen for 10 min at -78 C and dimethyl sulfide (20 mL) was added at that temperature. The dry ice bath was replaced with an ice bath and the mixture was stirred for 1 h at 0 C. The solvent was removed in vacuo and the crude product was dissolved in benzene (125 mL). To the solution MeOH (19.0 mL) and p-toluenesulfonic acid (58 mg, 3.1 mmol) were added and the mixture was stirred at 25 C for 16 h. After evaporation of the solvent in vacuo, flash chromatography (6:1 hexanes/EtOAc eluent) provided benzyl ether 8 (3.65 g, 51% yield) as a pale yellow oil: IR (thin film/ NaCl) 3501 (m), 2993 (m), 2951 (s), 1732 (s), 1603 (w), 1586 (w), 1496 (m), 1454 (m), 1379 (m) cm-1; 1H NMR (400 MHz, CDCl3) ( 7.37-7.25 (m, 5H), 4.85 (d, J=5.1 Hz, 1H), 4.50 (s, 2H), 3.78 (s, 3H), 3.72 (br s, 1H), 3.57-3.49 (m, 2H), 3.46 (s, 3H), 3.37 (s, 3H), 2.60 (m, 1H), 1.86 (m, 1H), 1.77 (m, 1H), 1.26 (s, 3H); 13C NMR (100 MHz, CDCl3) ( 171.8, 137.9, 128.3, 127.7, 127.6, 108.5, 104.4, 87.0, 73.0, 68.7, 56.4, 52.5, 50.5, 48.8, 26.8, 16.3; HRMS (EI) m/z 323.1503 [calc'd for C17H23O6 (M-CH3OH+H) 323.1495]. ________________________________________________________________ Preparation of ketone 5a and 5b.  EMBED ChemDraw.Document.4.5  The procedure for providing 6 was followed using ()-3-pentene-2-ol (2) (E:Z=23:1 mixture) (1.00 g, 11.6 mmol) and methyl 2-diazo-3-oxo-butanoate (1.50 g, 10.6 mmol) to afford a mixture of diastereomers 5a/5b (ca.7:1) (1.53 g, 66% yield) as a pale yellow oil. These diastereomers were difficult to separate, thus characterization was carried out as mixture: IR (thin film/NaCl) 3488 (br m), 3028 (m), 2971 (m), 2938 (m), 2880 (m), 2857 (m), 1722 (s), 1670 (w), 1451 (m), 1437 (m), 1356 (m) cm-1; 1H NMR (500 MHz, CDCl3) ( 5.59-5.47 (m, 1H), 5.32 (m, 0.88H), 5.22 (m, 0.12H), 4.22 (br s, 0.12H), 4.09 (br s, 0.88H), 3.78 (s, 0.36H), 3.73 (s, 2.64H), 3.19-3.10 (m, 1H), 2.32 (s, 2.64H), 2.27 (s, 0.36H), 1.61 (dd, J=1.4, 6.5 Hz, 2.64H), 1.59 (dd, J=1.5, 6.6 Hz, 0.36H), 1.01 (d, J=6.4 Hz, 0.36H), 0.87 (d, J=7.1 Hz, 2.64H); 13C NMR (100 MHz, CDCl3) ( 205.3/204.9, 170.8/170.7, 129.8/129.2, 127.6/127.8, 87.7/87.5, 53.2, 42.9/43.0, 25.5/25.0, 17.9/17.9, 14.3/15.7 ; HRMS (EI) m/z 201.1132 [calc'd for C10H17O4 (M+H) 201.1127]. ________________________________________________________________ Preparation of alcohol 7.  EMBED ChemDraw.Document.4.5  The procedure for providing 8 was followed using diastereomeric mixture of alcohols 5a/5b (ca.7:1)(6.55 g, 37.9 mmol) to afford a diastereomeric mixture of alcohols (5.58 g, 61% yield) as a colorless oil. A major single diastereomer 7 (2.42g, 27% yield) was isolated by flash chromatography (1:1 pentane/Et2O) as a pale yellow oil: IR (thin film/NaCl) 3503 (s), 2990, (s), 2952 (s), 2913 (s), 2835 (m), 1756 (s), 1732 (s), 1462 (s), 1391 (s) cm-1; 1H NMR (500 MHz, CDCl3) ( 4.77 (d, J=6.5 Hz, 1H), 3.84 (s, 3H), 3.49 (s, 3H), 3.36 (s, 3H), 2.54 (app p, J=6.6 Hz, 1H), 1.26 (s, 3H), 1.05 (d, J=6.7 Hz, 3H); 13C NMR (125 MHz, CDCl3) ( 171.6, 109.2, 104.1, 87.4, 56.5, 52.4, 48.7, 47.2, 16.3, 9.7; HRMS (CI) m/z 203.0918 [calc'd for C9H15O5 (M-CH3OH+H) 203.0919] This major diastereomer was used for next step. ________________________________________________________________ Preparation of alcohol 9. EMBED ChemDraw.Document.4.5 A mixture of benzyl ether 9 (3.12 g, 8.81 mmol) and 10% Pd-C (600 mg) in MeOH (80 mL) was stirred for 7 h under H2 atmosphere. The mixture was filtered through Celite and the filtrate was evaporated to give a white solid. Crystallization from hexanes/EtOAc provided alcohol 9 (1.83 g, 79% yield) as colorless crystals. Crystals suitable for X-ray analysis were obtained by recrystallization from hexanes/EtOAc: mp 116-117 C (dec); IR (thin film/NaCl) 3436 (br s), 3281 (br m), 2949 (s), 2896 (m), 2838 (m), 1744 (s), 1443 (m), 1391 (s) cm-1; 1H NMR (400 MHz, CDCl3) ( 4.87 (d, J=6.2 Hz, 1H), 3.81 (s, 3H), 3.79 (br s, 1H), 3.70-3.59 (m, 2H), 3.47 (s, 3H), 3.34 (s, 3H), 2.79-2.61 (br, 1H), 2.56 (app q, J=6.6 Hz, 1H), 1.78-1.63 (m, 2H), 1.24 (s, 3H); 13C NMR (100 MHz, CDCl3) ( 171.4, 108.1, 104.3, 86.8, 61.5, 56.4, 52.6, 51.1, 48.8, 29.1, 16.3; HRMS (EI) m/z 201.0765 [calc'd for C9H13O5 (M-2x(CH3OH)+H) 201.0763]. ________________________________________________________________ Preparation of selenyl compound 10. EMBED ChemDraw.Document.4.5 To a stirred solution of alcohol 9 (150 mg, 0.568 mmol) and 2-nitrophenyl selenocyanate (155 mg, 0.683 mmol) at -15 C in THF (6.5 mL) was added tri-n-butylphosphine (0.170 mL, 0.682 mmol) dropwise. The reaction mixture was allowed to warm to 0 C over 2.5 h. After evaporation of the solvent in vacuo, the residue was purified by flash chromatography (2:1 then 1:1 hexanes/EtOAc eluent) to provide selenyl compound 10 (252 mg, 99% yield) as a yellow solid. Crystallization from hexanes/EtOAc/CH2Cl2 afforded 10 as yellow crystals: mp 108-109; IR (thin film/NaCl) 3501 (m), 2992 (m), 2948 (m), 2835 (m), 1732 (s), 1590 (m), 1566 (m), 1513 (s), 1451 (m) cm-1; 1H NMR (400 MHz, CDCl3) ( 8.27 (dd, J=1.5, 8.6 Hz, 1H), 7.52 (m, 1H), 7.45 (dd, J=1.3, 8.0 Hz, 1H), 7.30 (m, 1H), 4.86 (d, J=6.3 Hz, 1H), 3.83 (s, 3H), 3.49 (s, 3H), 3.46 (br s, 1H), 3.37 (s, 3H), 3.02-2.88 (m, 2H), 2.67 (m, 1H), 1.99-1.86 (m, 2H), 1.25 (s, 3H); 13C NMR (100 MHz, CDCl3) ( 171.4, 146.7, 133.6, 133.0, 128.7, 126.3, 125.3, 108.0, 104.3, 87.1, 56.4, 52.9, 52.8, 48.9, 25.9, 23.5, 16.1; HRMS (FAB) m/z 449.0588 [calc'd for C17H23NO880Se (M) 449.0589]. ________________________________________________________________ Preparation of olefin 11. EMBED ChemDraw.Document.4.5 To a stirred ice-cooled solution of 10 (97.1 mg, 0.217 mmol) in THF (4.0 mL) was added a 30% H2O2 solution (0.50 mL). After 1 h stirring, the mixture was warmed to 35 C and the stirring was continued another 4 h at that temperature. The mixture was cooled to 0 C and saturated aqueous Na2S2O3 solution was added. The mixture was extracted with EtOAc (3 x 12 mL) and the combined organic layers were washed with H2O (20 mL), brine (20 mL), dried over Na2SO4, and concentrated in vacuo. Purification by flash chromatography (4:1 hexanes/EtOAc eluent) provided olefin 11 (35.4 mg, 66% yield) as a pale yellow oil: IR (thin film/NaCl) 3501 (s), 3084 (w), 2993 (s), 2952 (s), 2836 (m), 1757 (s), 1732 (s), 1642 (w), 1445 (s), 1383 (s) cm-1; 1H NMR (400 MHz, CDCl3) ( 5.69 (m, 1H), 5.28 (dd, J=1.0, 17.2 Hz, 1H), 5.20 (dd, J=1.0, 10.0 Hz, 1H), 4.98 (d, J=5.9 Hz, 1H), 3.81 (s, 3H), 3.47 (s, 3H), 3.46 (br s, 1H), 3.35 (s, 3H), 3.12 (app t, J=7.1 Hz, 1H), 1.24 (s, 3H); 13C NMR (100 MHz, CDCl3) ( 171.3, 131.0, 120.8, 107.1, 104.3, 87.6, 57.0, 56.6, 52.7, 48.8, 16.1; HRMS (CI) m/z 215.0919 [calc'd for C10H15O5 (M-CH3OH+H) 215.0919]. ________________________________________________________________ Preparation of alcohol 12. EMBED ChemDraw.Document.4.5 A mixture of 10 (1.18 g, 2.63 mmol) and Ra-Ni (6 g) (washed by decantation with H2O (15 times) and THF (5 times)) in THF (45 mL) was stirred for 2 h under H2 atmosphere. The mixture was filtered through Celite and the filtrate was evaporated to a residue. Purification by flash chromatography (4:1 then 3:1 hexanes/EtOAc eluent) provided alcohol 12 (546 mg, 84% yield) as a colorless oil: IR (thin film/NaCl) 3502 (m), 2963 (m), 2878 (m), 1756 (m), 1732 (s), 1463 (m), 1443 (m), 1382 (m) cm-1; 1H NMR (400 MHz, CDCl3) ( 4.75 (d, J=6.3 Hz, 1H), 3.81 (s, 3H), 3.46 (s, 3H), 3.38 (br s, 1H), 3.34 (s, 3H), 2.37 (dt, J=9.4, 6.3 Hz, 1H), 1.52 (m, 1H), 1.41 (m, 1H), 1.23 (s, 3H), 0.94 (t, J=7.5 Hz, 3H); 13C NMR (100 MHz, CDCl3) ( 171.8, 108.9, 104.2, 87.3, 56.3, 53.9, 52.5, 48.7, 19.7, 16.0, 12.3; HRMS (CI) m/z 217.1066 [calc'd for C10H17O5 (M-CH3OH+H) 217.1076]. ________________________________________________________________ Preparation of acetate 13. EMBED ChemDraw.Document.4.5 A mixture of alcohol 9 (360 mg, 1.36 mmol), pyridine (1.0 mL), and Ac2O (1.0 mL) was kept at 25 C for 3 h. Toluene (5 mL) was added and the mixture was evaporated (repeated 3 times) to a residue. Purification by flash chromatography (1:1 hexanes/EtOAc eluent) provided acetate 13 (405 mg, 97% yield) as a colorless oil: IR (thin film/NaCl) 3493 (br m), 2992 (m), 2953 (m), 2836 (m), 1738 (s), 1443 (m), 1369 (m) cm-1; 1H NMR (400 MHz, CDCl3) ( 4.82 d, J=6.4, 1H), 4.15-3.99 (m, 2H), 3.83 (s, 3H), 3.45 (s, 3H), 3.41 (br s, 1H), 3.34 (s, 3H), 2.55 (dt, J=9.0, 6.4 Hz, 1H), 2.02 (s, 3H), 1.89-1.69 (m, 2H), 1.23 (s, 3H); 13C NMR (100 MHz, CDCl3) ( 171.5, 170.8, 108.2, 104.2, 87.0, 62.4, 56.4, 52.7, 49.7, 48.8, 25.7, 20.9, 16.2; HRMS (CI) m/z 275.1134 [calc'd for C12H19O7 (M-CH3OH+H) 275.1131]. ________________________________________________________________ Preparation of alcohol 15. EMBED ChemDraw.Document.4.5 A stirred solution of indolocarbazole 14 (128 mg, 0.500 mmol) and camphorsulfonic acid (27 mg, 0.12 mmol) in 1,2-dichloroethane (20 mL) was heated at reflux and treated over 16 h with a solution of 7 (400 mg, 1.71 mmol) in 1,2-dichloroethane (5.0 mL). After an additional 24 h, the reaction mixture was allowed to cool to room temperature, diluted with CH2Cl2 (8 mL), and washed with saturated aqueous NaHCO3 (10 mL). The aqueous layer was extracted with CH2Cl2 (2 x 5 mL), and the combined organic layers were dried over Na2SO4 and evaporated in vacuo. Flash chromatography (3:1 hexanes/EtOAc eluent) provided alcohol 15 (188 mg, 89% yield). Crystals suitable for X-ray analysis were obtained by recrystallization from pentane/EtOAc: 15: mp 229-231C; IR (thin film/NaCl) 3497 (s), 3049 (s), 2955 (s), 1727 (s), 1639 (s), 1569 (s), 1457 (s), 1440 (s), 1393 (s), 1312 (s) cm-1; 1H NMR (500 MHz, CDCl3) ( 8.19-8.17 (m, 2H), 7.98 (s, 2H), 7.72 (d, J=10.9 Hz, 1H), 7.53-7.45 (m, 2H), 7.41 (app t, J=9.2 Hz, 1H), 7.33-7.27 (m, 2H), 6.43 (d, J=8.0 Hz, 1H), 4.08 (s, 3H), 3.85 (s, 1H), 2.82 (app q, J=7.5 Hz, 1H), 2.19 (s, 3H), 1.21 (d, J=8.5 Hz, 3H); 13C NMR (100 MHz, CDCl3) ( 173.0, 139.5, 137.4, 126.9, 126.3, 124.9, 124.9, 124.7, 121.0, 120.8, 120.1, 119.8, 119.5, 113.5, 112.5, 112.2, 107.6, 98.2, 90.3, 88.3, 53.5, 48.0, 22.2,10.9; HRMS (FAB) m/z 426.1571 [calc'd for C26H22N2O4 (M) 426.1566]. ________________________________________________________________ Preparation of acetate 19. EMBED ChemDraw.Document.4.5 To a stirred suspension of indolocarbazole 14 (157 mg, 0.613 mmol) and acetate 13 (376 mg, 1.23 mmol) in 1,2-dichloroethane (20 mL) was added camphorsulfonic acid (14.2 mg, 0.0611 mmol). After heating at reflux for 36 h, the reaction mixture was allowed to cool to room temperature, and washed with saturated aqueous NaHCO3 (10 mL). The aqueous layer was extracted with CH2Cl2 (2 x 7 mL), and the combined organic layers were dried over Na2SO4 and evaporated in vacuo. Purification by flash chromatography (3:1 then 2:1 hexanes/EtOAc eluent) provided acetate 19 (252 mg, 83% yield) as a pale yellow powder: IR (thin film/NaCl) 3479 (br m), 3051 (m), 3003 (m), 2955 (m), 1732 (s), 1639 (m), 1569 (m), 1458 (m), 1440 (s) cm-1; 1H NMR (400 MHz, CDCl3) ( 8.21-8.14 (m, 2H), 8.03-7.95 (m, 2H), 7.73 (d, J=8.2 Hz, 1H), 7.54-7.47 (m, 3H), 7.30 (app t, J=7.3 Hz, 2H), 6.50 (d, J=6.2 Hz, 1H), 4.13 (s, 3H), 4.01 (m, 1H), 3.92 (s, 1H), 3.71 (m, 1H), 2.88 (m, 1H), 2.18 (s, 3H), 2.13 (m, 1H), 2.03 (m, 1H), 1.71 (s, 3H); 13C NMR (100 MHz, CDCl3) ( 172.8, 170.4, 139.5, 137.0, 126.8, 126.3, 125.0, 124.8, 124.7, 124.7, 121.1, 120.9, 120.8, 120.2, 120.0, 119.7, 113.5, 112.6, 112.4, 107.7, 98.5, 89.4, 87.7, 61.9, 53.7, 50.7, 26.8, 22.2, 20.4; HRMS (FAB) m/z 498.1791 [calc'd for C29H26N2O6 (M) 498.1791]. ________________________________________________________________ Preparation of alcohol 16. EMBED ChemDraw.Document.4.5 The procedure for providing acetate 19 was followed using indolocarbazole 14 (103 mg, 0.402 mmol) and alcohol 12 (200 mg, 0.806 mmol) to afford alcohol 16 (167 mg, 94% yield) as a white solid. Crystals of 16 suitable for X-ray analysis were obtained by recrystallization from pentane/EtOAc: m.p. 230-231C; IR (thin film/NaCl) 3495 (s), 3048 (m), 2966 (m), 1727 (s), 1639 (m), 1569 (m), 1458 (s), 1440 (s), 1387 (s) cm-1; 1H NMR (400 MHz, CDCl3) ( 8.22-8.17 (m, 2H), 8.04-7.98 (m, 2H), 7.72 (d, J=8.4 Hz, 1H), 7.53-7.45 (m, 2H), 7.42 (app t, J=8.3 Hz, 1H), 7.35-7.27 (m, 2H), 6.45 (d, J=6.0 Hz, 1H), 4.12 (s, 3H), 3.89 (s, 1H), 2.72 (app q, J=7.5 Hz, 1H), 2.17 (s, 3H), 1.82-1.69 (m, 2H), 0.78 (t, J=7.7 Hz, 3H); 13C NMR (100 MHz, CDCl3) ( 173.3, 139.5, 136.8, 126.9, 126.3, 124.9, 124.8, 124.7, 124.7, 121.0, 120.8, 120.8, 120.1, 119.8, 119.4, 113.6, 112.5, 112.2, 108.0, 98.3, 89.9, 88.1, 54.7, 53.6, 22.1, 20.9, 12.4; HRMS (FAB) m/z 440.1734 [calc'd for C27H24N2O4 (M) 440.1736]. ________________________________________________________________ Preparation of benzyl olefin 17. EMBED ChemDraw.Document.4.5 The procedure for providing acetate 19 was followed using indolocarbazole 14 (20.0 mg, 0.0781 mmol) and olefin 11 (38.8 mg, 0.158 mmol) to afford olefin 17 (18.7 mg, 55% yield) as a pale yellow powder: IR (thin film/NaCl) 3488 (m), 3048 (m), 2953 (m), 2925 (m), 1730 (s), 1639 (m), 1569 (m), 1458 (s), 1441 (s) cm-1; 1H NMR (400 MHz, CDCl3) ( 8.21-8.14 (m, 2H), 8.03-7.97 (m, 2H), 7.73 (d, J=8.6 Hz, 1H), 7.50-7.38 (m, 3H), 7.35-7.25 (m, 2H), 6.68 (d, J=5.5 Hz, 1H), 5.96 (ddd, J=8.0, 10.4, 16.8 Hz, 1H), 5.21 (app d, J=10.4 Hz, 1H), 5.05 (app d, J=16.8 Hz, 1H), 4.11 (s, 3H), 3.94 (s, 1H), 3.41 (dd, J=5.5, 8.0 Hz, 1H), 2.20 (s, 3H); 13C NMR (100 MHz, CDCl3) ( 172.7, 139.5, 137.3, 130.1, 126.7, 126.3, 124.9, 124.8, 124.7, 122.5, 121.1, 120.9, 120.7, 120.2, 119.9, 119.6, 113.5, 112.6, 112.3, 107.9, 98.2, 88.6, 88.5, 57.6, 53.7, 22.2; HRMS (FAB) m/z 438.1578 [calc'd for C27H22N2O4 (M) 438.1580]. ________________________________________________________________ Preparation of benzyl ether 18. EMBED ChemDraw.Document.4.5 The procedure for providing acetate 19 was followed using indolocarbazole 14 (109 mg, 0.426 mmol) and benzyl ether 8 (302 mg, 0.853 mmol) to afford benzyl ether 18 (105 mg, 45% yield) as a pale yellow powder: IR (thin film/NaCl) 3484 (br m), 3056 (m), 2951 (m), 2867 (m), 1731 (s), 1638 (m), 1569 (m), 1493 (s), 1457 (s), 1440 (s) cm-1; 1H NMR (400 MHz, CDCl3) ( 8.18 (d, J=4.8 Hz, 1H), 8.16 (d, J=4.8 Hz, 1H), 8.04-7.95 (m, 2H), 7.79 (d, J=8.6 Hz, 1H), 7.53-7.38 (m, 3H), 7.35-7.21 (m, 5H), 7.12-7.03 (m, 2H), 6.53 (d, J=6.1 Hz, 1H), 4.35 (s, 1H), 4.21 (d, J=11.8 Hz, 1H), 4.15 (d, J=11.8 Hz, 1H), 3.95 (s, 3H), 3.40 (m, 1H), 3.19 (m, 1H), 2.85 (m, 1H), 2.26 (m, 1H), 2.13 (s, 3H), 1.92 (m, 1H); 13C NMR (100 MHz, CDCl3) ( 172.3, 139.6, 137.3, 136.9, 128.3, 127.8, 127.7, 127.0, 126.2, 124.9, 124.8, 124.7, 121.0, 120.8, 120.7, 120.0, 119.8, 119.5, 113.9, 112.5, 112.3, 107.8, 99.0, 89.9, 87.8, 73.1, 68.5, 53.1, 52.9, 27.7, 22.4; HRMS (FAB) m/z 546.2157 [calc'd for C34H30N2O5 (M) (FAB) 546.2155]. ________________________________________________________________ Chemical correlation of 16 - 20.  EMBED ChemDraw.Document.4.5  ________________________________________________________________ Preparation of alcohol 20. EMBED ChemDraw.Document.4.5 A solution of acetate 19 (248 mg, 0.498 mmol) in MeOH (13 mL) was treated with K2CO3 (103 mg, 0.745 mmol) at 25 C. After 40 min stirring, the mixture was concentrated under reduced pressure to half of the original volume. The mixture was poured into EtOAc (30 mL) and washed with H2O (20 mL) then the aqueous layer was extracted with EtOAc (2 x 10 mL). The combined organic layers were washed with H2O (20 mL), brine (30 mL), dried over Na2SO4, and evaporated to a residue. Purification by flash chromatography (3:2 hexanes/EtOAc eluent) afforded alcohol 20 (217 mg, 96% yield) as a white powder: IR (thin film/NaCl) 3476 (br m), 3049 (m), 2952 (m), 1730 (s), 1638 (m), 1569 (m), 1492 (m), 1458 (s), 1440 (s) cm-1; 1H NMR (400 MHz, CDCl3) ( 8.18-8.11 (m, 2H), 8.01-7.93 (m, 2H), 7.77 (d, J=8.7 Hz, 1H), 7.53-7.36 (m, 3H), 7.32-7.23 (m, 2H), 6.53 (d, J=6.2 Hz, 1H), 4.58 (s, 1H), 4.07 (s, 3H), 3.62 (m, 1H), 3.31 (m, 1H), 2.85 (m, 1H), 2.19 (s, 3H), 2.14 (m, 1H), 1.93 (m, 1H), 1.67 (br, 1H); 13C NMR (100 MHz, CDCl3) ( 172.4, 139.5, 137.2, 126.9, 126.2, 124.9, 124.8, 124.7, 124.6, 120.9, 120.7, 120.7, 120.0, 119.8, 119.5, 113.7, 112.5, 112.2, 107.7, 98.9, 89.7, 87.6, 60.5, 53.0, 52.5, 29.6, 22.3; HRMS (FAB) m/z 456.1686 [calc'd for C27H24N2O5 (M) 456.1685]. ________________________________________________________________ Preparation of alcohol 20. EMBED ChemDraw.Document.4.5 A mixture of benzyl ether 18 (28.1 mg, 0.0515 mmol) and 10% Pd-C (6 mg) in MeOH (2.5 mL) was stirred under H2 atmosphere. Additional 10% Pd-C (5 mg) was added every 2 days and stirring was continued for 10 days. The mixture was filtered through Celite and the filtrate was evaporated, purified by flash chromatography (2:1 hexanes/EtOAc eluent) to afford alcohol 20 (16.7 mg, 71% yield) as a white powder. ________________________________________________________________ Preparation of selenyl compound 32. EMBED ChemDraw.Document.4.5 The procedure for providing selenyl compound 10 was followed using 20 (70.8 mg, 0.155 mmol) to afford selenyl compound 32 (85.3 mg, 86% yield) as a yellow solid. Crystals for data analysis were obtained by recrystallization from hexanes/EtOAc: m.p. >235 C (dec); IR (thin film/NaCl) 3485 (m), 3055 (w), 2953 (w), 1727 (s), 1638 (w), 1590 (m), 1567 (m), 1510 (s), 1457 (m), 1439 (s) cm-1; 1H NMR (400 MHz, CDCl3) ( 8.24-8.16 (m, 3H), 8.03 (d, J=8.3 Hz, 1H), 7.95 (d, J=8.3 Hz, 1H), 7.71 (d, J=8.1 Hz, 1H), 7.50-7.38 (m, 3H), 7.36-7.21 (m, 4H), 6.95-6.88 (m, 1H), 6.50 (d, J=6.1 Hz, 1H), 4.12 (s, 3H), 3.96 (s, 1H), 2.92 (m, 1H), 2.73 (dt, J=11.8, 5.2 Hz, 1H), 2.48 (dt, J=11.8, 6.1 Hz, 1H), 2.19 (s, 3H), 2.19-2.02 (m, 2H); 13C NMR (100 MHz, CDCl3) ( 172.8, 146.4, 139.4, 136.7, 133.6, 132.3, 128.5, 126.8, 126.3, 126.3, 125.4, 125.0, 124.9, 124.7, 121.2, 121.0, 120.9, 120.2, 120.0, 119.7, 113.4, 112.6, 112.5, 107.8, 98.2, 89.1, 87.8, 53.9, 53.9, 26.2, 23.2, 22.1; HRMS (FAB) m/z 641.1068 [calc'd for C33H27N3O680Se (M) 641.1065]. ________________________________________________________________ Preparation of alcohol 16. EMBED ChemDraw.Document.4.5 The procedure for providing alcohol 12 was followed using selenyl compond 32 (64.9 mg, 0.101 mmol) to afford alcohol 16 (39.5 mg, 89% yield) as a white solid. ________________________________________________________________ Preparation of alcohol 16. EMBED ChemDraw.Document.4.5 The procedure for providing alcohol 9 was followed using olefin 17 (7.8 mg, 0.018 mmol) and 10% Pd-C (1.5 mg) to afford alcohol 16 (7.8 mg, quant.) as a white solid. ________________________________________________________________ Preparation of indolocarbazole 23 and 24. EMBED ChemDraw.Document.4.5 A stirred solution of 6-N-DMB-staurosporinone (21) (75.0 mg, 0.163 mmol) and camphorsulfonic acid (3.8 mg, 0.0164 mmol) in 1,2-dichloroethane (5.4 mL) was heated at reflux and treated over 24 h with a solution of alcohol 7 (84.0 mg, 0.359 mmol) in 1,2-dichloroethane (3.6 mL) using a syringe pump. After an additional 48 h, the reaction mixture was allowed to cool to room temperature, diluted with CH2Cl2 (8 mL), and washed with saturated aqueous NaHCO3 (10 mL). The aqueous layer was extracted with CH2Cl2 (2 x 5 mL), and the combined organic layers were dried over Na2SO4 and evaporated in vacuo. Flash chromatography (40:1 (70%CH2Cl2/hexanes)/MeOH eluent) followed by preparative TLC (60:1 (70%CH2Cl2/hexanes)/MeOH 10 elutions) provided indolocarbazole 23 (40.6 mg, 40% yield) and 24 (9.6 mg, 9.4% yield). Crystals of 23 suitable for X-ray analysis were obtained by recrystallization from acetone-d6. 23: mp 270-272 C (dec); IR (thin film/NaCl) 3485 (br m), 3303 (br m), 3052 (m), 2998 (m), 2953 (m), 2835 (m), 1731 (s), 1673 (s), 1649 (s), 1590 (m), 1515 (s), 1459 (s), 1397 (s) cm-1; 1H NMR (400 MHz, acetone-d6) ( 9.38 (d, J=8.0 Hz, 1H), 7.98 (d, J=8.2 Hz, 1H), 7.93 (d, J=7.5 Hz, 1H), 7.79 (d, J=8.2 Hz, 1H), 7.44 (app t, J=7.6 Hz, 1H), 7.41 (app t, J=6.7 Hz, 1H), 7.33-7.20 (m, 2H), 7.03 (d, J=1.1 Hz, 1H), 6.97-6.84 (m, 2H), 6.74 (d, J=6.1 Hz, 1H), 5.44 (s, 1H), 4.94 (d, J=17.4 Hz, 1H), 4.89 (d, J=17.4 Hz, 1H), 4.82 (d, J=14.6 Hz, 1H), 4.72 (d, J=14.6 Hz, 1H), 4.04 (s, 3H), 3.75 (s, 3H), 3.75 (s, 3H), 2.87 (m, 1H), 2.18 (s, 3H), 1.31 (d, J=6.8 Hz, 3H); 13C NMR (100 MHz, acetone-d6) ( 172.2, 169.7, 150.3, 149.5, 141.0, 138.5, 131.5, 131.1, 129.7, 127.0, 126.4, 125.6, 125.5, 125.3, 123.9, 121.8, 121.1, 120.8, 120.4, 120.2, 117.2, 115.6, 115.5, 112.5, 112.5, 108.6, 100.2, 91.0, 89.4, 55.8, 55.8, 53.0, 50.2, 49.6, 46.2, 22.7, 11.1; HRMS (FAB) m/z 632.2398 [calc'd for C37H34N3O7 (M+H) 632.2397]. 24: IR (thin film/NaCl) 3484 (br m), 3322 (br m), 3051 (m), 2954 (m), 2836 (m), 1732 (s), 1673 (s), 1591 (m), 1515 (s), 1455 (s), 1403 (s), 1349 (s) cm-1; 1H NMR (400 MHz, acetone-d6) ( 9.70 (d, J=7.6 Hz, 1H), 8.01 (d, J=7.9 Hz, 1H), 7.94 (d, J=8.8 Hz, 1H), 7.87 (d, J=8.8 Hz, 1H), 7.51 (app t, J=7.5 Hz, 1H), 7.42 (app t, J=7.6 Hz, 1H), 7.30 (app t, J=7.5 Hz, 1H), 7.29 (app t, J=7.3 Hz, 1H), 7.07 (d, J=1.8 Hz, 1H), 6.99 (dd, J=1.8, 8.1 Hz, 1H), 6.92 (d, J=8.1 Hz, 1H), 6.74 (d, J=6.2 Hz, 1H), 5.36 (s, 1H), 5.01-4.92 (AB-q, 2H), 4.91-4.83 (AB-q, 2H), 4.04 (s, 3H), 3.77 (s, 6H), 2.85 (m, 1H), 2.19 (s, 3H), 1.29 (d, J=7.1 Hz, 3H); 13C NMR (100 MHz, acetone-d6) ( 172.1, 170.0, 150.3, 149.5, 140.8, 138.6, 131.6, 131.6, 127.7, 127.6, 126.9, 126.2, 125.8, 125.8, 123.5, 122.4, 121.0, 120.9, 120.8, 120.3, 118.0, 115.2, 114.9, 112.5, 112.5, 109.3, 100.1, 90.9, 89.6, 55.8, 55.8, 53.0, 49.7, 49.7, 46.3, 22.8, 11.0; HRMS (FAB) m/z 631.2319 [calc'd for C37H33N3O7 (M) 631.2319]. ________________________________________________________________ Preparation of indolocarbazole 25.  EMBED ChemDraw.Document.4.5  The procedure for providing indolocarbazole 23/24 was followed using 21 (100 mg, 0.217 mmol) and alcohol 12 (119 mg, 0.480 mmol) to afford indolocarbazole 25 (30.4 mg, 22% yield) as a pale yellow powder: IR (thin film/NaCl) 3485 (br m), 3390 (m), 3051 (m), 2960 (m), 2928 (m), 2853 (m), 1731 (s), 1673 (s), 1591 (m), 1514 (s), 1459 (s) cm-1; 1H NMR (400 MHz, acetone-d6) ( 9.45 (d, J=7.8 Hz, 1H), 7.98 (d, J=8.5 Hz, 1H), 7.94 (d, J=7.8 Hz, 1H), 7.82 (d, J=8.4 Hz, 1H), 7.51 (app t, J=8.1 Hz, 1H), 7.41 (app t, J=7.4 Hz, 1H), 7.29 (app t, J=7.7 Hz, 1H), 7.26 (app t, J=7.9 Hz, 1H), 7.06 (d, J=1.6 Hz, 1H), 6.97 (dd, J=1.6, 8.3 Hz, 1H), 6.91 (d, J=8.3 Hz, 1H), 6.78 (d, J=6.0 Hz, 1H), 5.37 (s, 1H), 4.97-4.93 (AB-q, 2H), 4.85 (br s, 2H), 4.04 (s, 3H), 3.76 (s, 3H), 3.75 (s, 3H), 2.69 (m, 1H), 2.17 (s, 3H), 1.89-1.62 (m, 2H), 0.77 (t, J=7.5 Hz, 3H); 13C NMR (100 MHz, acetone-d6) ( 172.3, 169.8, 150.3, 149.5, 141.0, 137.9, 131.6, 131.1, 129.7, 127.2, 126.2, 125.6, 125.5, 125.3, 124.1, 121.8, 121.1, 120.8, 120.5, 120.2, 117.3, 115.7, 115.6, 112.5, 112.5, 109.1, 100.1, 90.5, 89.3, 56.4, 55.9, 55.8, 53.1, 50.2, 46.3, 22.5, 21.1, 12.8; HRMS (FAB) m/z 646.2552 [calc'd for C38H36N3O3 (M+H) 646.2553]. ________________________________________________________________ Preparation of indolocarbazole 26.  EMBED ChemDraw.Document.4.5  A stirred solution of 6-N-DMB-staurosporinone (21) (73.0 mg, 0.158 mmol) and camphorsulfonic acid (3.7 mg, 0.016 mmol) in 1,2-dichloroethane (5.3 mL) was heated at reflux and treated over 24 h with a solution of acetate 13 (169 mg, 0.552 mmol) in 1,2-dichloroethane (5.5 mL) by using syringe pump. After an additional 65 h, the reaction mixture was allowed to cool to room temperature, diluted with CH2Cl2 (8 mL), and washed with saturated aqueous NaHCO3 solution (10 mL). The aqueous layer was extracted with CH2Cl2 (2 x 5 mL), and the combined organic layers were dried over Na2SO4 and evaporated in vacuo. Flash chromatography (50:1 (70%CH2Cl2/hexanes)/ MeOH eluent) followed by preparative TLC (40:1 (70%CH2Cl2/hexanes)/MeOH 8 elutions) provided indolocarbazole 26 (20.8 mg, 19% yield): IR (thin film/NaCl) 3475 (br m), 3052 (m), 2999 (m), 2954 (m), 2836 (m), 1738 (s), 1674 (s), 1652 (s), 1591 (m), 1515 (s), 1459 (s), 1396 (m) cm-1; 1H NMR (500 MHz, acetone-d6) ( 9.46 (d, J=7.5 Hz, 1H), 8.02-7.96 (m, 2H), 7.86 (d, J=8.6 Hz, 1H), 7.51 (app t, J=7.7 Hz, 1H), 7.43 (app t, J=7.8 Hz, 1H), 7.31 (app t, J=7.4 Hz, 1H), 7.30 (app t, J=7.2 Hz, 1H), 7.09 (d, J=1.8 Hz, 1H), 7.00 (dd, J=2.0, 8.2 Hz, 1H), 6.93 (d, J=8.3 Hz, 1H), 6.81 (d, J=5.9 Hz, 1H), 5.39 (s, 1H), 5.11-4.93 (AB-q, 2H), 4.90 (br s, 2H), 4.07 (s, 3H), 3.98 (m, 1H), 3.83 (m, 1H), 3.77 (s, 3H), 3.77 (s, 3H), 2.95 (m, 1H), 2.23-2.12 (m, 2H), 2.18 (s, 3H), 1.55 (s, 3H); 13C NMR (100 MHz, CDCl3) ( 172.4, 170.5, 169.6, 149.3, 148.4, 140.0, 137.2, 130.1, 130.1, 128.9, 126.6, 125.9, 125.2, 124.8, 124.5, 123.3, 121.1, 120.8, 120.2, 120.1, 119.7, 117.1, 114.9, 114.4, 111.0, 110.9, 107.1, 99.1, 89.5, 88.0, 61.8, 55.9, 55.8, 53.7, 51.0, 49.6, 46.0, 27.1, 22.5, 20.5; HRMS (FAB) m/z 704.2614 [calc'd for C40H38N3O9 (M+H) 704.2608]. ________________________________________________________________ Preparation of C2-methyl-K252a (29). EMBED ChemDraw.Document.4.5 To a stirred solution of indolocarbazole 23 (23.9 mg, 0.0379 mmol) in CH2Cl2 (2.0 mL) at 25 C was added anisole (0.206 mL, 1.90 mmol) followed by 2,2,2-trifluoroacetic acid (2.0 mL). After 7.5 h stirring, the reaction mixture was cooled in ice bath, diluted with CH2Cl2 (15 mL), and saturated aqueous NaHCO3 (15 mL) was added carefully. The layers were separated and the aqueous layer was extracted with CH2Cl2 (2 x 5 mL). The combined organic layers were dried over Na2SO4 and evaporated in vacuo. Purification by preparative TLC (60:1 (70%CH2Cl2/hexanes)/MeOH 10 elutions) afforded C2-methyl-K252a (29) (11.6 mg, 64% yield) as a pale yellow powder: IR (thin film/NaCl) 3399 (br m), 2957 (m), 2929 (m), 2880 (w), 1734 (s), 1670 (s), 1588 (w), 1458 (s), 1395 (m) cm-1; 1H NMR (400 MHz, acetone-d6) ( 9.38 (d, J=8.6 Hz, 1H), 8.05 (d, J=7.9 Hz, 1H), 8.01 (d, J=8.9 Hz, 1H), 7.81 (d, J=8.3 Hz, 1H), 7.61 (br s, 1H), 7.49 (app t, J=7.8 Hz, 1H), 7.45 (app t, J=7.8 Hz, 1H), 7.34 (app t, J=7.6 Hz, 1H), 7.28 (app t, J=7.5 Hz, 1H), 6.75 (d, J=5.8 Hz, 1H), 5.41 (s, 1H), 5.10 (br s, 2H), 4.05 (s, 3H), 2.83 (m, 1H), 2.20 (s, 3H), 1.29 (d, J=7.1 Hz, 3H); 13C NMR (100 MHz, acetone-d6) ( 172.7, 172.2, 140.9, 138.5, 133.9, 133.9, 129.9, 127.1, 126.3, 125.6, 125.5, 124.1, 121.9, 121.2, 120.6, 120.2, 117.3, 115.8, 115.6, 108.6, 100.2, 91.0, 89.3, 53.0, 49.6, 46.3, 22.7, 11.0; HRMS (FAB) m/z 482.1717 [calc'd for C28H24N3O5 (M+H) 482.1716]. ________________________________________________________________ Preparation of C2-ethyl-K252a (30). EMBED ChemDraw.Document.4.5 To a stirred solution of indolocarbazole 25 (25.0 mg, 0.0388 mmol) in CH2Cl2 (2.0 mL) at 25 C was added anisole (0.422 mL, 3.88 mmol) followed by 2,2,2-trifluoroacetic acid (2.0 mL). After 7.5 h stirring, the reaction mixture was cooled in ice bath, diluted with CH2Cl2 (15 mL), and saturated aqueous NaHCO3 (15 mL) was added carefully. The layers were separated and the aqueous layer was extracted with CH2Cl2 (2 x 5 mL). The combined organic layers were dried over Na2SO4 and evaporated in vacuo. Purification by preparative TLC (60:1 (70%CH2Cl2/hexanes)/MeOH 10 elutions) afforded C2-ethyl-K252a (30) (12.1 mg, 63% yield) as a pale yellow powder: IR (KBr pellet) 3426 (br m), 3216 (br m), 3051 (m), 2961 (m), 2927 (m), 2874 (m), 1732 (s), 1668 (s), 1632 (s), 1590 (m), 1458 (m) cm-1; 1H NMR (400 MHz, acetone-d6) ( 9.40 (d, J=7.5 Hz, 1H), 8.05 (d, J=8.0 Hz, 1H), 8.01 (d, J=8.4 Hz, 1H), 7.82 (d, J=8.1 Hz, 1H), 7.60 (br s, 1H), 7.51 (app t, J=7.8 Hz, 1H), 7.45 (app t, J=7.2 Hz, 1H), 7.34 (app t, J=7.6 Hz, 1H), 7.28 (app t, J=7.2 Hz, 1H), 6.78 (d, J=6.1 Hz, 1H), 5.34 (s, 1H), 5.10 (br s, 2H), 4.05 (s, 3H), 2.67 (m, 1H), 2.19 (s, 3H), 1.88 (m, 1H), 1.79 (m, 1H), 0.76 (t, J=7.5 Hz, 3H); 13C NMR (100 MHz, DMSO-d6) ( 171.8, 171.2, 139.9, 136.6, 133.1, 128.7, 125.8, 125.5, 125.1, 124.3, 124.2, 122.6, 121.3, 120.5, 119.6, 119.5, 115.8, 115.2, 114.6, 109.2, 99.6, 89.5, 88.3, 55.7, 52.5, 45.6, 22.2, 20.0, 12.7; HRMS (FAB) m/z 496.1874 [calc'd for C29H26N3O5 (M+H) 496.1872]. ________________________________________________________________ Preparation of C2-(2-hydroxyethyl)-K252a (31). EMBED ChemDraw.Document.4.5 To a stirred solution of indolocarbazole 26 (11.4 mg, 0.0162 mmol) in CH2Cl2 (0.80 mL) at 25 C was added anisole (0.176 mL, 1.62 mmol) followed by 2,2,2-trifluoroacetic acid (0.80 mL). After 10 h stirring, the reaction mixture was cooled in ice bath, diluted with CH2Cl2 (10 mL), and saturated aqueous NaHCO3 (10 mL) was added carefully. The layers were separated and the aqueous layer was extracted with CH2Cl2 (2 x 5 mL). The combined organic layers were dried over Na2SO4 and evaporated in vacuo to afford a slightly brown solid. The solid was dissolved in MeOH (2.0 mL) and CH2Cl2 (1.0 mL) followed by treatment with K2CO3 (3.5 mg, 0.0253 mmol, 1.6 eq) at 25 C. After 3 h stirring, the mixture was poured into brine (5.0 mL) and extracted with CH2Cl2 (3 x 8 mL). The combined organic layers were dried over Na2SO4, evaporated and purified by preparative TLC (20:1 (70%CH2Cl2/hexanes)/MeOH 5 elutions) to provide C2-(2-hydroxyethyl)-K252a (31) (5.1 mg, 62% yield in 2 steps): IR (KBr pellet) 3322 (br m), 3051 (m), 2951 (m), 2869 (m), 1731 (m), 1661 (m), 1590 (m), 1460 (m) cm-1; 1H NMR (400 MHz, DMSO-d6) ( 9.20 (d, J=7.8 Hz, 1H), 8.64 (s, 1H), 8.04 (d, J=7.7 Hz, 1H), 7.97 (d, J=8.5 Hz, 1H), 7.93 (d, J=8.4 Hz, 1H), 7.48 (app t, J=8.5 Hz, 1H), 7.46 (app t, J=8.6 Hz, 1H), 7.35 (app t, J=7.4 Hz, 1H), 7.27 (app t, J=7.5 Hz, 1H), 6.82 (d, J=5.8 Hz, 1H), 6.37 (s, 1H), 5.05-4.95 (AB-q, 2H), 4.34 (m, 1H), 3.94 (s, 3H), 3.28 (m, 1H), 2.99 (m, 1H), 2.64 (m, 1H), 2.09 (s, 3H), 1.89 (m, 1H), 1.80 (m, 1H); 13C NMR (100 MHz, DMSO-d6) ( 171.8, 171.3, 139.9, 136.9, 133.1, 128.7, 125.8, 125.5, 125.1, 124.3, 124.2, 122.6, 121.3, 120.5, 119.7, 119.5, 115.9, 115.2, 114.6, 109.1, 99.4, 89.4, 88.3, 58.9, 52.6, 50.9, 45.6, 30.4, 22.3; HRMS (FAB) m/z 512.1828 [calc'd for C29H26N3O6 (M+H) 512.1822]. ________________________________________________________________ In vitro Kinase Assay To determine the IC50 of K252a and its derivatives for PAK and a few other kinases, the assay was conducted at 25oC in the presence of 100 uM peptide substrate(s) and 10 uM ATP, and at various concentrations of each test compound. PAK assay was performed, using the GST-PAK3 fusion protein purified from E. coli which is constitutively activated, and its specific peptide substrate PC9 as previously described1. PKA (c-AMP-dependent kinase) assay was carried out, using the purified catalytic subunit of PKA (Sigma Chemicals) and its specific substrate "kemptide" (Sigma Chemicals) as described previously2,3. PKC (Ca/phospholipid/TPA-dependent kinase) assay was conducted, using purified rat brain PKC (a gift of Drs. Belinda Michell and Bruce Kemp) and its specific peptide substrate derived from EGF receptor (Sigma Chemicals) in the presence of its activators, i.e., 0.1 mM Ca, 20 ug/ml phophatidylserine (PS) and 10 ng/ml TPA as described previously4. References (In vitro Kinase Assay) 1. Brzeska, H., Lynch, T., Martin, B., Corigliano-Murphy, A. & Korn, E. D. J. Biol. Chem. 265, 16138-16144 (1990). 2. a) Maroney, A., Glicksman, M., Basma, A., Walton, K. et al J. Neurosci. 18, 104-111 (1998). b) Kitagawa, M., Okabe, T., Ogino, H. et al Oncogene 8, 425-2432 (1993). 3. Kase, H., Iwahashi, K., Nakanishi, S., Matsuda, Y., Yamada, K., Tkahashi, M., Murakata, C., Sato, A. & Kaneko, M. Biochem. Biophys. Res. Comm. 142, 436-440 (1987). 4. Castagna, M., Takai, Y., Kaibuchi, K., Sano, K., Kikkawa, U. & Nishizuka, Y. J. Biol. Chem. 257, 7847-7851 (1982). ________________________________________________________________ Appendix  EMBED ChemDraw.Document.4.5  X-ray Structure report Data Collection A colorless prism crystal of CADVANCE \d311ADVANCE \u3HADVANCE \d320ADVANCE \u3OADVANCE \d37ADVANCE \u3 having approximate dimensions of 0.20 x 0.24 x 0.24 mm was mounted on a glass fiber. All measurements were made on an Nonius KappaCCD diffractometer with graphite monochromated Mo-K radiation. Cell constants and an orientation matrix for data collection, obtained from a least-squares refinement using ten (1o in , 10s exposure, de-zingered) data frames, corresponded to a primitive triclinic cell with dimensions: a = 7.1314(2)  = 82.269(2)ADVANCE \u3oADVANCE \d3 b = 8.0930(2)  = 78.113(2)ADVANCE \u3oADVANCE \d3 c = 11.6224(3)  = 73.421(2) V = 627.05(3) ADVANCE \u33ADVANCE \d3 For Z = 2 and F.W. = 264.27, the calculated density is 1.40 g/cmADVANCE \u33ADVANCE \d3. Based on a statistical analysis of intensity distribution, and the successful solution and refinement of the structure, the space group was determined to be: P-1 (#2). The data were collected at a temperature of -90 + 1ADVANCE \u3oADVANCE \d3C to a maximum 2 value of 54.9ADVANCE \u3oADVANCE \d3. Six omega scans consisting of 55, 51, 33, 51, 55 and 55 data frames, respectively, were collected with a scan width of 2.0o and a detector-to-crystal distance, Dx, of 33mm. Each frame was exposed twice (for the purpose of de-zingering) for 40s. The data frames were processed and scaled using the DENZO software package. (Z. Otwinowski and W. Minor, Processing of X-Ray Diffraction Data Collected in Oscillation Mode, Methods in Enzymology, vol. 276: Macromolecular Crystallography, part A, 307-326, 1997, C.W. Carter, Jr. & R.M. Sweet, Eds., Academic Press). Data Reduction Of the 5346 reflections which were collected, 2869 were unique (RADVANCE \d1intADVANCE \u1 = 0.016); equivalent reflections were merged. No decay correction was applied. The linear absorption coefficient, , for Mo-K radiation is 1.2 cmADVANCE \u3-1ADVANCE \d3 and no absorption correction was applied. Structure Solution and Refinement The structure was solved by direct methodsADVANCE \u31ADVANCE \d3 and expanded using Fourier techniquesADVANCE \u32ADVANCE \d3. The non-hydrogen atoms were refined anisotropically. Hydrogen atoms were refined isotropically. The final cycle of full-matrix least-squares refinementADVANCE \u33ADVANCE \d3 was based on 2064 observed reflections (I > 5.00(I)) and 243 variable parameters and converged (largest parameter shift was 0.00 times its esd) with unweighted and weighted agreement factors of: R =  ||Fo| - |Fc|| /  |Fo| = 0.036 RADVANCE \d1wADVANCE \u1 = [(  w (|Fo| - |Fc|)ADVANCE \u32ADVANCE \d3 /  w FoADVANCE \u32ADVANCE \d3)]ADVANCE \u31/2ADVANCE \d3 = 0.044 The standard deviation of an observation of unit weightADVANCE \u34ADVANCE \d3 was 2.33. The weighting scheme was based on counting statistics and included a factor (p = 0.010) to downweight the intense reflections. Plots of  w (|Fo| - |Fc|)ADVANCE \u32ADVANCE \d3 versus |Fo|,,reflection order in data collection, sin /, and various classes of indices showed no unusual trends. The maximum and minimum peaks on the final difference Fourier map corresponded to 0.23 and -0.28 eADVANCE \u3-ADVANCE \d3/ADVANCE \u33ADVANCE \d3, respectively. Neutral atom scattering factors were taken from Cromer and WaberADVANCE \u35ADVANCE \d3. Anomalous dispersion effects were included in FcalcADVANCE \u36ADVANCE \d3; the values for f' and f" were those of Creagh and McAuleyADVANCE \u37ADVANCE \d3. The values for the mass attenuation coefficients are those of Creagh and HubbelADVANCE \u38ADVANCE \d3. All calculations were performed using the teXsanADVANCE \u39ADVANCE \d3 crystallographic software package of Molecular Structure Corporation. EXPERIMENTAL DETAILS A. Crystal Data Empirical Formula CADVANCE \d311ADVANCE \u3HADVANCE \d320ADVANCE \u3OADVANCE \d37ADVANCE \u3 Formula Weight 264.27 Crystal Color, Habit colorless, prism Crystal Dimensions 0.20 X 0.24 X 0.24 mm Crystal System triclinic Lattice Type Primitive Lattice Parameters a = 7.1314(2) b = 8.0930(2) c = 11.6224(3)  = 82.269(2)ADVANCE \u3oADVANCE \d3  = 78.113(2)ADVANCE \u3oADVANCE \d3  = 73.421(2)ADVANCE \u3oADVANCE \d3 V = 627.05(3) ADVANCE \u33ADVANCE \d3 Space Group P-1 (#2) Z value 2 DADVANCE \d1calcADVANCE \u1 1.400 g/cmADVANCE \u33ADVANCE \d3 FADVANCE \d1000ADVANCE \u1 284.00 (MoK) 1.17 cmADVANCE \u3-1ADVANCE \d3 B. Intensity Measurements Diffractometer Nonius KappaCCD Radiation MoK ( = 0.71069 ) graphite monochromated Take-off Angle 2.8ADVANCE \u3oADVANCE \d3 Crystal to Detector Distance 33 mm Temperature -90.0ADVANCE \u3oADVANCE \d3C Scan Rate 40s/frame Scan Width 2ADVANCE \u3oADVANCE \d3/frame 2ADVANCE \d1maxADVANCE \u1 54.9ADVANCE \u3oADVANCE \d3 No. of Reflections Measured Total: 5346 Unique: 2869 (RADVANCE \d1intADVANCE \u1 = 0.016) Corrections Lorentz-polarization C. Structure Solution and Refinement Structure Solution Direct Methods (SIR92) Refinement Full-matrix least-squares Function Minimized  w (|Fo| - |Fc|)ADVANCE \u32ADVANCE \d3 Least Squares Weights 1/ADVANCE \u32ADVANCE \d3(Fo) p-factor 0.0100 Anomalous Dispersion All non-hydrogen atoms No. Observations (I>5.00(I)) 2064 No. Variables 243 Reflection/Parameter Ratio 8.49 Residuals: R; Rw 0.036 ; 0.044 Goodness of Fit Indicator 2.33 Max Shift/Error in Final Cycle 0.00 Maximum peak in Final Diff. Map 0.23 eADVANCE \u3-ADVANCE \d3/ADVANCE \u33ADVANCE \d3 Minimum peak in Final Diff. Map -0.28 eADVANCE \u3-ADVANCE \d3/ADVANCE \u33ADVANCE \d3 Table 1. Atomic coordinates and BADVANCE \d1isoADVANCE \u1/BADVANCE \d1eqADVANCE \u1 atom x y z BADVANCE \d1eqADVANCE \u1 O(1) 0.7177(1) 0.1222(1) 0.37658(8) 1.72(2) O(2) 0.9322(1) 0.3014(1) 0.31919(8) 2.04(2) O(3) 0.7797(2) 0.1140(1) 0.00198(9) 2.53(3) O(4) 0.6795(2) -0.0223(1) 0.17492(9) 2.34(2) O(5) 0.8763(1) 0.3434(1) 0.10272(10) 2.26(2) O(6) 0.0758(1) 0.5774(1) 0.14022(10) 2.41(2) O(7) 0.4505(1) 0.3521(1) 0.44663(8) 2.01(2) C(1) 0.8719(2) 0.1614(2) 0.2888(1) 1.71(3) C(2) 0.7714(2) 0.2376(2) 0.1801(1) 1.68(3) C(3) 0.5646(2) 0.3400(2) 0.2403(1) 1.67(3) C(4) 0.5285(2) 0.2375(2) 0.3587(1) 1.66(3) C(5) 1.0451(2) 0.0029(2) 0.2719(2) 2.35(4) C(6) 0.9591(3) 0.2880(3) 0.4391(1) 2.47(4) C(7) 0.7486(2) 0.1022(2) 0.1076(1) 1.75(3) C(8) 0.6490(3) -0.1544(2) 0.1133(2) 2.50(4) C(9) 0.3978(2) 0.3817(2) 0.1676(1) 2.00(3) C(10) 0.2335(2) 0.5398(2) 0.2057(1) 2.07(3) C(11) 0.4067(3) 0.2699(2) 0.5619(1) 2.41(4) H(1) 0.583(2) 0.449(2) 0.257(1) 1.6(3) H(2) 0.437(2) 0.162(2) 0.362(1) 1.2(3) H(3) 1.003(2) -0.095(2) 0.260(1) 2.9(4) H(4) 1.139(2) 0.029(2) 0.205(2) 3.4(4) H(5) 1.115(2) -0.026(2) 0.342(1) 3.1(4) H(6) 1.037(2) 0.369(2) 0.442(1) 2.6(3) H(7) 0.835(3) 0.312(2) 0.490(2) 3.7(4) H(8) 1.042(3) 0.170(3) 0.461(2) 3.6(4) H(9) 0.756(3) -0.180(3) 0.042(2) 4.8(5) H(10) 0.521(3) -0.112(3) 0.085(2) 5.0(5) H(11) 0.643(3) -0.256(3) 0.170(2) 5.8(5) H(12) 0.871(4) 0.354(4) 0.027(3) 10.7(9) H(13) 0.451(2) 0.405(2) 0.087(2) 2.5(3) H(14) 0.340(2) 0.280(2) 0.176(1) 2.4(3) H(15) 0.281(2) 0.644(2) 0.194(1) 2.4(3) H(16) 0.179(2) 0.530(2) 0.295(2) 2.7(3) H(17) 0.027(5) 0.488(5) 0.146(3) 12(1) H(18) 0.326(3) 0.363(2) 0.617(2) 4.1(4) H(19) 0.331(3) 0.184(3) 0.562(2) 3.9(4) H(20) 0.527(3) 0.208(2) 0.595(2) 4.3(4) BADVANCE \d1eqADVANCE \u1 = 8/3 ADVANCE \u32ADVANCE \d3(UADVANCE \d111ADVANCE \u1(aa*)ADVANCE \u32ADVANCE \d3 + UADVANCE \d122ADVANCE \u1(bb*)ADVANCE \u32ADVANCE \d3 + UADVANCE \d133ADVANCE \u1(cc*)ADVANCE \u32ADVANCE \d3 + 2UADVANCE \d112ADVANCE \u1(aa*bb*)cos  + 2UADVANCE \d113ADVANCE \u1(aa*cc*)cos  + 2UADVANCE \d123ADVANCE \u1(bb*cc*)cos ) ________________________________________________________________  EMBED ChemDraw.Document.4.5  X-ray Structure report Data Collection A colorless prism crystal of CADVANCE \d326ADVANCE \u3HADVANCE \d322ADVANCE \u3NADVANCE \d32ADVANCE \u3OADVANCE \d34ADVANCE \u3 having approximate dimensions of 0.12 x 0.20 x 0.25 mm was mounted on a glass fiber. All measurements were made on a Nonius KappaCCD diffractometer with graphite monochromated Mo-K radiation. Cell constants and an orientation matrix for data collection, obtained from a least-squares refinement using ten (1o in , 10s exposure, de-zingered) data frames, corresponded to a primitive monoclinic cell with dimensions: a = 9.2658(3) , b = 20.771(1) ,  = 93.659(2)ADVANCE \u3oADVANCE \d3, c = 10.8824(4) , V = 2090.2(1) ADVANCE \u33ADVANCE \d3. For Z = 4 and F.W. = 426.47, the calculated density is 1.36 g/cmADVANCE \u33ADVANCE \d3. The systematic absences of: h0l: h = 2n+1, 0k0: k = 2n+1; uniquely determine the space group to be: P2ADVANCE \d31ADVANCE \u3/a (#14). The data were collected at a temperature of -90 + 1ADVANCE \u3oADVANCE \d3C to a maximum 2 value of 55.1ADVANCE \u3oADVANCE \d3. Four omega scans consisting of 82, 74, 74 and 82 data frames, respectively, were collected with a scan width of 1.4o and a detector-to-crystal distance, Dx, of 35mm. Each frame was exposed twice (for the purpose of de-zingering) for 28s. The data frames were processed and scaled using the DENZO software package. (Z. Otwinowski and W. Minor, Processing of X-Ray Diffraction Data Collected in Oscillation Mode, Methods in Enzymology, vol. 276: Macromolecular Crystallography, part A, 307-326, 1997, C.W. Carter, Jr. & R.M. Sweet, Eds., Academic Press). Data Reduction A total of 4925 reflections was collected. No decay correction was applied. The linear absorption coefficient, , for Mo-K radiation is 0.9 cmADVANCE \u3-1ADVANCE \d3 and no absorption correction was applied. The data were corrected for Lorentz and polarization effects. Structure Solution and Refinement The structure was solved by direct methodsADVANCE \u31ADVANCE \d3 and expanded using Fourier techniquesADVANCE \u32ADVANCE \d3. The non-hydrogen atoms were refined anisotropically. Hydrogen atoms were refined isotropically. The final cycle of full-matrix least-squares refinementADVANCE \u33ADVANCE \d3 was based on 2850 observed reflections (I > 3.00(I)) and 377 variable parameters and converged (largest parameter shift was 0.00 times its esd) with unweighted and weighted agreement factors of: R =  ||Fo| - |Fc|| /  |Fo| = 0.043 RADVANCE \d1wADVANCE \u1 = [(  w (|Fo| - |Fc|)ADVANCE \u32ADVANCE \d3 /  w FoADVANCE \u32ADVANCE \d3)]ADVANCE \u31/2ADVANCE \d3 = 0.044 The standard deviation of an observation of unit weightADVANCE \u34ADVANCE \d3 was 2.07. The weighting scheme was based on counting statistics and included a factor (p = 0.020) to downweight the intense reflections. Plots of  w (|Fo| - |Fc|)ADVANCE \u32ADVANCE \d3 versus |Fo|, reflection order in data collection, sin / and various classes of indices showed no unusual trends. The maximum and minimum peaks on the final difference Fourier map corresponded to 0.25 and -0.19 eADVANCE \u3-ADVANCE \d3/ADVANCE \u33ADVANCE \d3, respectively. Neutral atom scattering factors were taken from Cromer and WaberADVANCE \u35ADVANCE \d3. Anomalous dispersion effects were included in FcalcADVANCE \u36ADVANCE \d3; the values for f' and f" were those of Creagh and McAuleyADVANCE \u37ADVANCE \d3. The values for the mass attenuation coefficients are those of Creagh and HubbelADVANCE \u38ADVANCE \d3. All calculations were performed using the teXsanADVANCE \u39ADVANCE \d3 crystallographic software package of Molecular Structure Corporation. EXPERIMENTAL DETAILS A. Crystal Data Empirical Formula CADVANCE \d326ADVANCE \u3HADVANCE \d322ADVANCE \u3NADVANCE \d32ADVANCE \u3OADVANCE \d34ADVANCE \u3 Formula Weight 426.47 Crystal Color, Habit colorless, prism Crystal Dimensions 0.12 X 0.20 X 0.25 mm Crystal System monoclinic Lattice Type Primitive Lattice Parameters a = 9.2658(3) b = 20.771(1) c = 10.8824(4)  = 93.659(2)ADVANCE \u3oADVANCE \d3 V = 2090.2(1) ADVANCE \u33ADVANCE \d3 Space Group P2ADVANCE \d31ADVANCE \u3/a (#14) Z value 4 DADVANCE \d1calcADVANCE \u1 1.355 g/cmADVANCE \u33ADVANCE \d3 FADVANCE \d1000ADVANCE \u1 896.00 (MoK) 0.92 cmADVANCE \u3-1ADVANCE \d3 B. Intensity Measurements Diffractometer Nonius KappaCCD Radiation MoK ( = 0.71069 ) graphite monochromated Take-off Angle 2.8ADVANCE \u3oADVANCE \d3 Crystal to Detector Distance 35 mm Temperature -90.0ADVANCE \u3oADVANCE \d3C Scan Type  Scan Rate 28s/frame Scan Width 1.4ADVANCE \u3oADVANCE \d3 2ADVANCE \d1maxADVANCE \u1 55.1ADVANCE \u3oADVANCE \d3 No. of Reflections Measured Total: 4925 Corrections Lorentz-polarization C. Structure Solution and Refinement Structure Solution Direct Methods (SIR92) Refinement Full-matrix least-squares Function Minimized  w (|Fo| - |Fc|)ADVANCE \u32ADVANCE \d3 Least Squares Weights 1/ADVANCE \u32ADVANCE \d3(Fo) p-factor 0.0200 Anomalous Dispersion All non-hydrogen atoms No. Observations (I>3.00(I)) 2850 No. Variables 377 Reflection/Parameter Ratio 7.56 Residuals: R; Rw 0.043 ; 0.044 Goodness of Fit Indicator 2.07 Max Shift/Error in Final Cycle 0.00 Maximum peak in Final Diff. Map 0.25 eADVANCE \u3-ADVANCE \d3/ADVANCE \u33ADVANCE \d3 Minimum peak in Final Diff. Map -0.19 eADVANCE \u3-ADVANCE \d3/ADVANCE \u33ADVANCE \d3 Table 1. Atomic coordinates and BADVANCE \d1isoADVANCE \u1/BADVANCE \d1eqADVANCE \u1 atom x y z BADVANCE \d1eqADVANCE \u1 O(1) 0.8274(1) 0.35796(5) 0.6880(1) 2.68(3) O(2) 0.8012(2) 0.50039(7) 0.5064(1) 3.54(3) O(3) 0.5836(2) 0.52924(7) 0.6381(1) 4.88(4) O(4) 0.6335(1) 0.45231(6) 0.7774(1) 3.54(3) N(1) 0.8764(2) 0.37325(6) 0.4807(1) 2.54(4) N(2) 1.0745(2) 0.36424(7) 0.7318(1) 2.75(4) C(1) 0.8414(2) 0.36510(8) 0.3543(2) 2.55(4) C(2) 0.7217(2) 0.38491(10) 0.2809(2) 3.35(5) C(3) 0.7152(2) 0.36926(10) 0.1574(2) 3.77(6) C(4) 0.8256(2) 0.33505(10) 0.1051(2) 3.63(5) C(5) 0.9467(2) 0.31730(9) 0.1764(2) 3.01(5) C(6) 0.9571(2) 0.33305(8) 0.3015(2) 2.42(4) C(7) 1.0693(2) 0.32342(8) 0.3976(2) 2.41(4) C(8) 1.0154(2) 0.34849(8) 0.5052(2) 2.36(4) C(9) 1.2079(2) 0.29531(8) 0.3988(2) 2.60(5) C(10) 1.2917(2) 0.29093(8) 0.5066(2) 2.79(5) C(11) 1.2397(2) 0.31500(8) 0.6163(2) 2.66(4) C(12) 1.1029(2) 0.34451(8) 0.6144(2) 2.51(4) C(13) 1.2955(2) 0.31643(8) 0.7437(2) 2.75(4) C(14) 1.4221(2) 0.29366(9) 0.8054(2) 3.23(5) C(15) 1.4420(3) 0.30189(9) 0.9309(2) 3.70(6) C(16) 1.3372(2) 0.33255(10) 0.9967(2) 3.81(6) C(17) 1.2108(2) 0.35607(10) 0.9390(2) 3.37(5) C(18) 1.1905(2) 0.34725(8) 0.8121(2) 2.77(4) C(19) 0.9385(2) 0.39499(8) 0.7523(2) 2.72(4) C(20) 0.9281(2) 0.46358(9) 0.6991(2) 3.06(5) C(21) 0.7900(2) 0.46224(8) 0.6125(2) 2.80(4) C(22) 0.7768(2) 0.38953(8) 0.5781(2) 2.63(4) C(23) 0.9383(3) 0.5157(1) 0.7969(2) 4.28(6) C(24) 0.6573(2) 0.48494(9) 0.6762(2) 3.23(5) C(25) 0.5047(3) 0.4701(1) 0.8378(3) 4.97(7) C(26) 0.6245(2) 0.3657(1) 0.5462(2) 3.17(5) H(1) 0.644(2) 0.4088(8) 0.313(2) 3.2(4) H(2) 0.633(2) 0.3814(8) 0.108(2) 3.8(5) H(3) 0.814(2) 0.3232(9) 0.017(2) 4.2(5) H(4) 1.026(2) 0.2940(8) 0.142(2) 2.9(4) H(5) 1.242(2) 0.2791(8) 0.327(1) 2.4(4) H(6) 1.383(2) 0.2709(8) 0.508(1) 2.7(4) H(7) 1.498(2) 0.2745(8) 0.759(1) 3.1(4) H(8) 1.532(2) 0.2853(8) 0.974(2) 4.0(5) H(9) 1.358(2) 0.3390(8) 1.085(2) 3.6(4) H(10) 1.137(2) 0.3771(8) 0.981(2) 3.1(4) H(11) 0.923(2) 0.3914(7) 0.844(2) 2.8(4) H(12) 1.007(2) 0.4693(7) 0.646(1) 2.7(4) H(13) 0.853(3) 0.508(1) 0.862(2) 6.2(6) H(14) 1.036(3) 0.5160(10) 0.830(2) 4.8(5) H(15) 0.915(2) 0.557(1) 0.759(2) 6.4(6) H(16) 0.726(2) 0.532(1) 0.516(2) 5.3(5) H(17) 0.500(3) 0.440(1) 0.903(2) 6.6(6) H(18) 0.519(3) 0.515(1) 0.867(2) 6.5(6) H(19) 0.418(3) 0.467(1) 0.776(2) 9.2(9) H(20) 0.564(2) 0.3988(9) 0.494(2) 4.2(4) H(21) 0.573(2) 0.3617(8) 0.626(2) 3.7(4) H(22) 0.627(2) 0.3224(10) 0.505(2) 4.9(5) BADVANCE \d1eqADVANCE \u1 = 8/3 ADVANCE \u32ADVANCE \d3(UADVANCE \d111ADVANCE \u1(aa*)ADVANCE \u32ADVANCE \d3 + UADVANCE \d122ADVANCE \u1(bb*)ADVANCE \u32ADVANCE \d3 + UADVANCE \d133ADVANCE \u1(cc*)ADVANCE \u32ADVANCE \d3 + 2UADVANCE \d112ADVANCE \u1(aa*bb*)cos  + 2UADVANCE \d113ADVANCE \u1(aa*cc*)cos  + 2UADVANCE \d123ADVANCE \u1(bb*cc*)cos ) ________________________________________________________________  EMBED ChemDraw.Document.4.5  X-ray Structure report Data Collection A colorless plate crystal of CADVANCE \d327ADVANCE \u3HADVANCE \d324ADVANCE \u3NADVANCE \d32ADVANCE \u3OADVANCE \d34ADVANCE \u3 having approximate dimensions of 0.12 x 0.21 x 0.25 mm was mounted on a glass fiber. All measurements were made on a Nonius KappaCCD diffractometer with graphite monochromated Mo-K radiation. Cell constants and an orientation matrix for data collection, obtained from a least-squares refinement using ten (1o in , 10s exposure, de-zingered) data frames, corresponded to a primitive monoclinic cell with dimensions: a = 9.2213(3) , b = 21.886(1) ,  = 92.073(2)ADVANCE \u3oADVANCE \d3, c = 10.7661(4) , and V = 2171.3(1) ADVANCE \u33ADVANCE \d3. For Z = 4 and F.W. = 440.50, the calculated density is 1.35 g/cmADVANCE \u33ADVANCE \d3. The systematic absences of: h0l: h = 2n+1, 0k0: k = 2n+1; uniquely determine the space group to be: P2ADVANCE \d31ADVANCE \u3/a (#14). The data were collected at a temperature of -90 + 1ADVANCE \u3oADVANCE \d3C to a maximum 2 value of 54.9ADVANCE \u3oADVANCE \d3. Three omega scans consisting of 69, 64 and 69 data frames, respectively, were collected with a scan width of 1.6o and a detector-to-crystal distance, Dx, of 33mm. Each frame was exposed twice (for the purpose of de-zingering) for 16s. The data frames were processed and scaled using the DENZO software package. (Z. Otwinowski and W. Minor, Processing of X-Ray Diffraction Data Collected in Oscillation Mode, Methods in Enzymology, vol. 276: Macromolecular Crystallography, part A, 307-326, 1997, C.W. Carter, Jr. & R.M. Sweet, Eds., Academic Press). Data Reduction A total of 5088 reflections was collected. No decay correction was applied. The linear absorption coefficient, , for Mo-K radiation is 0.9 cmADVANCE \u3-1ADVANCE \d3 and no absorption correction was applied. The data were corrected for Lorentz and polarization effects. Structure Solution and Refinement The structure was solved by direct methodsADVANCE \u31ADVANCE \d3 and expanded using Fourier techniquesADVANCE \u32ADVANCE \d3. The non-hydrogen atoms were refined anisotropically. Some hydrogen atoms were refined isotropically, the rest were included in fixed positions. In the case of the methyl group hydrogen atoms, one hydrogen was located in the difference map and included at an idealized distance to set the orientation of the other two hydrogen atoms. The final cycle of full-matrix least-squares refinementADVANCE \u33ADVANCE \d3 was based on 2338 observed reflections (I > 3.00(I)) and 302 variable parameters and converged (largest parameter shift was 0.00 times its esd) with unweighted and weighted agreement factors of: R =  ||Fo| - |Fc|| /  |Fo| = 0.045 RADVANCE \d1wADVANCE \u1 = [(  w (|Fo| - |Fc|)ADVANCE \u32ADVANCE \d3 /  w FoADVANCE \u32ADVANCE \d3)]ADVANCE \u31/2ADVANCE \d3 = 0.042 The standard deviation of an observation of unit weightADVANCE \u34ADVANCE \d3 was 1.75. The weighting scheme was based on counting statistics and included a factor (p = 0.020) to downweight the intense reflections. Plots of  w (|Fo| - |Fc|)ADVANCE \u32ADVANCE \d3 versus |Fo|, reflection order in data collection, sin /, and various classes of indices showed no unusual trends. The maximum and minimum peaks on the final difference Fourier map corresponded to 0.22 and -0.24 eADVANCE \u3-ADVANCE \d3/ADVANCE \u33ADVANCE \d3, respectively. Neutral atom scattering factors were taken from Cromer and WaberADVANCE \u35ADVANCE \d3. Anomalous dispersion effects were included in FcalcADVANCE \u36ADVANCE \d3; the values for f' and f" were those of Creagh and McAuleyADVANCE \u37ADVANCE \d3. The values for the mass attenuation coefficients are those of Creagh and HubbelADVANCE \u38ADVANCE \d3. All calculations were performed using the teXsanADVANCE \u39ADVANCE \d3 crystallographic software package of Molecular Structure Corporation. EXPERIMENTAL DETAILS A. Crystal Data Empirical Formula CADVANCE \d327ADVANCE \u3HADVANCE \d324ADVANCE \u3NADVANCE \d32ADVANCE \u3OADVANCE \d34ADVANCE \u3 Formula Weight 440.50 Crystal Color, Habit colorless, plate Crystal Dimensions 0.12 X 0.21 X 0.25 mm Crystal System monoclinic Lattice Type Primitive Lattice Parameters a = 9.2213(3) b = 21.886(1) c = 10.7661(4)  = 92.073(2)ADVANCE \u3oADVANCE \d3 V = 2171.3(1) ADVANCE \u33ADVANCE \d3 Space Group P2ADVANCE \d31ADVANCE \u3/a (#14) Z value 4 DADVANCE \d1calcADVANCE \u1 1.347 g/cmADVANCE \u33ADVANCE \d3 FADVANCE \d1000ADVANCE \u1 928.00 (MoK) 0.91 cmADVANCE \u3-1ADVANCE \d3 B. Intensity Measurements Diffractometer Nonius KappaCCD Radiation MoK ( = 0.71069 ) graphite monochromated Take-off Angle 2.8ADVANCE \u3oADVANCE \d3 Crystal to Detector Distance 33 mm Temperature -90.0ADVANCE \u3oADVANCE \d3C Scan Rate 16s/frame Scan Width 1.6ADVANCE \u3oADVANCE \d3/frame 2ADVANCE \d1maxADVANCE \u1 54.9ADVANCE \u3oADVANCE \d3 No. of Reflections Measured Total: 5088 Corrections Lorentz-polarization C. Structure Solution and Refinement Structure Solution Direct Methods (SIR92) Refinement Full-matrix least-squares Function Minimized  w (|Fo| - |Fc|)ADVANCE \u32ADVANCE \d3 Least Squares Weights 1/ ADVANCE \u32ADVANCE \d3(Fo) p-factor 0.0200 Anomalous Dispersion All non-hydrogen atoms No. Observations (I>3.00(I)) 2338 No. Variables 302 Reflection/Parameter Ratio 7.74 Residuals: R; Rw 0.045 ; 0.042 Goodness of Fit Indicator 1.75 Max Shift/Error in Final Cycle 0.00 Maximum peak in Final Diff. Map 0.22 eADVANCE \u3-ADVANCE \d3/ADVANCE \u33ADVANCE \d3 Minimum peak in Final Diff. Map -0.24 eADVANCE \u3-ADVANCE \d3/ADVANCE \u33ADVANCE \d3 Table 1. Atomic coordinates and BADVANCE \d1isoADVANCE \u1/BADVANCE \d1eqADVANCE \u1 atom x y z BADVANCE \d1eqADVANCE \u1 O(1) -0.2985(2) -0.14364(7) -0.1815(1) 2.17(4) O(2) -0.2709(2) -0.00966(8) 0.0085(2) 2.90(5) O(3) -0.0448(2) 0.01271(10) -0.1306(2) 4.36(5) O(4) -0.1191(2) -0.05212(8) -0.2798(2) 3.00(4) N(1) -0.5467(2) -0.13898(9) -0.2169(2) 2.20(5) N(2) -0.3439(2) -0.13238(9) 0.0309(2) 2.03(5) C(1) -0.6610(2) -0.1570(1) -0.2957(2) 2.20(6) C(2) -0.6806(3) -0.1496(1) -0.4237(2) 2.62(7) C(3) -0.8056(3) -0.1734(1) -0.4790(2) 2.97(7) C(4) -0.9099(3) -0.2032(1) -0.4101(2) 2.92(7) C(5) -0.8902(3) -0.2108(1) -0.2834(2) 2.64(7) C(6) -0.7650(2) -0.1873(1) -0.2236(2) 2.21(6) C(7) -0.7090(2) -0.1880(1) -0.0959(2) 2.13(6) C(8) -0.7605(2) -0.2115(1) 0.0158(2) 2.35(6) C(9) -0.6763(2) -0.2064(1) 0.1230(2) 2.31(6) C(10) -0.5384(2) -0.1786(1) 0.1209(2) 1.97(6) C(11) -0.4248(2) -0.1702(1) 0.2145(2) 1.97(6) C(12) -0.4135(3) -0.1862(1) 0.3393(2) 2.49(6) C(13) -0.2880(3) -0.1722(1) 0.4077(2) 2.86(7) C(14) -0.1753(3) -0.1419(1) 0.3511(2) 2.82(7) C(15) -0.1828(3) -0.1258(1) 0.2273(2) 2.51(6) C(16) -0.3078(2) -0.1413(1) 0.1578(2) 2.03(6) C(17) -0.4858(2) -0.1549(1) 0.0106(2) 1.97(6) C(18) -0.5740(2) -0.1585(1) -0.0974(2) 1.98(6) C(19) -0.4125(2) -0.1073(1) -0.2392(2) 2.19(6) C(20) -0.4045(2) -0.0439(1) -0.1772(2) 2.37(6) C(21) -0.2614(2) -0.0457(1) -0.0998(2) 2.21(6) C(22) -0.2467(2) -0.1154(1) -0.0699(2) 2.14(6) C(23) -0.4254(3) 0.0100(1) -0.2662(2) 3.04(7) C(24) -0.5752(3) 0.0109(1) -0.3297(2) 3.68(7) C(25) -0.1310(3) -0.0242(1) -0.1709(2) 2.66(7) C(26) 0.0128(3) -0.0395(1) -0.3449(3) 4.53(8) C(27) -0.0928(2) -0.1379(1) -0.0456(2) 2.62(6) H(1) -0.6106 -0.1291 -0.4711 3.1482 H(2) -0.8212 -0.1693 -0.5663 3.5669 H(3) -0.9955 -0.2184 -0.4511 3.5086 H(4) -0.9608 -0.2318 -0.2374 3.1636 H(5) -0.8527 -0.2307 0.0171 2.8213 H(6) -0.7109 -0.2217 0.1989 2.7764 H(7) -0.4913 -0.2065 0.3774 2.9838 H(8) -0.2787 -0.1833 0.4929 3.4364 H(9) -0.0904 -0.1319 0.3994 3.3830 H(10) -0.1050 -0.1049 0.1904 3.0072 H(11) -0.3988 -0.1038 -0.3259 2.6290 H(12) -0.4808 -0.0420 -0.1202 2.8496 H(13) -0.3548 0.0074 -0.3281 3.6474 H(14) -0.4120 0.0469 -0.2206 3.6474 H(15) -0.5868 -0.0241 -0.3813 4.4196 H(16) -0.5855 0.0468 -0.3790 4.4196 H(17) -0.6470 0.0107 -0.2686 4.4196 H(18) 0.0167 0.0028 -0.3649 5.4383 H(19) 0.0134 -0.0629 -0.4192 5.4383 H(20) 0.0947 -0.0500 -0.2933 5.4383 H(21) -0.179(4) 0.006(2) 0.025(3) 11(1) H(22) -0.0408 -0.1092 0.0049 3.1450 H(23) -0.0949 -0.1762 -0.0042 3.1450 H(24) -0.0463 -0.1424 -0.1224 3.1450 BADVANCE \d1eqADVANCE \u1 = 8/3 ADVANCE \u32ADVANCE \d3(UADVANCE \d111ADVANCE \u1(aa*)ADVANCE \u32ADVANCE \d3 + UADVANCE \d122ADVANCE \u1(bb*)ADVANCE \u32ADVANCE \d3 + UADVANCE \d133ADVANCE \u1(cc*)ADVANCE \u32ADVANCE \d3 + 2UADVANCE \d112ADVANCE \u1(aa*bb*)cos  + 2UADVANCE \d113ADVANCE \u1(aa*cc*)cos  + 2UADVANCE \d123ADVANCE \u1(bb*cc*)cos ) ________________________________________________________________  EMBED ChemDraw.Document.4.5  X-ray Structure report Data Collection A pale yellow prism crystal of CADVANCE \d337ADVANCE \u3HADVANCE \d333ADVANCE \u3NADVANCE \d33ADVANCE \u3OADVANCE \d37ADVANCE \u3.CADVANCE \d31.5ADVANCE \u3OADVANCE \d30.5ADVANCE \u3 having approximate dimensions of 0.12 x 0.12 x 0.15 mm was mounted on a glass fiber. All measurements were made on a Nonius KappaCCD diffractometer with graphite monochromated Mo-K radiation. Cell constants and an orientation matrix for data collection, obtained from a least-squares refinement using ten (1o in , 10s exposure, de-zingered) data frames, corresponded to a primitive monoclinic cell with dimensions: a = 8.6682(2) , b = 22.6193(5) ,  = 96.219(1)ADVANCE \u3oADVANCE \d3, c = 17.3278(4) , and V = 3377.4(1) ADVANCE \u33ADVANCE \d3. For Z = 4 and F.W. = 657.70, the calculated density is 1.29 g/cmADVANCE \u33ADVANCE \d3. The systematic absences of: h0l: h+l = 2n+1, 0k0: k = 2n+1; uniquely determine the space group to be: P2ADVANCE \d31ADVANCE \u3/n (#14). The data were collected at a temperature of -90 + 1ADVANCE \u3oADVANCE \d3C to a maximum 2 value of 55.0ADVANCE \u3oADVANCE \d3. Three omega scans consisting of 69, 69 and 77 data frames, respectively, were collected with a scan width of 1.5o and a detector-to-crystal distance, Dx, of 35mm. Each frame was exposed twice (for the purpose of de-zingering) for 60s. The data frames were processed and scaled using the DENZO software package. (Z. Otwinowski and W. Minor, Processing of X-Ray Diffraction Data Collected in Oscillation Mode, Methods in Enzymology, vol. 276: Macromolecular Crystallography, part A, 307-326, 1997, C.W. Carter, Jr. & R.M. Sweet, Eds., Academic Press). Data Reduction A total of 7880 reflections was collected. No decay correction was applied. The linear absorption coefficient, , for Mo-K radiation is 0.9 cmADVANCE \u3-1ADVANCE \d3 and no absorption correction was applied. The data were corrected for Lorentz and polarization effects. Structure Solution and Refinement The structure was solved by direct methodsADVANCE \u31ADVANCE \d3 and expanded using Fourier techniquesADVANCE \u32ADVANCE \d3. The non-hydrogen atoms were refined anisotropically. Hydrogen atoms were refined isotropically. There is one disordered, 50% occupancy acetone solvent molecule in the asymmetric unit. The solvent is present in two overlapping (C38 is the overlapping carbon atom) orientations of 25% occupancy each. The final cycle of full-matrix least-squares refinementADVANCE \u33ADVANCE \d3 was based on 4027 observed reflections (I > 5.00(I)) and 619 variable parameters and converged (largest parameter shift was 0.10 times its esd) with unweighted and weighted agreement factors of: R =  ||Fo| - |Fc|| /  |Fo| = 0.048 RADVANCE \d1wADVANCE \u1 = [(  w (|Fo| - |Fc|)ADVANCE \u32ADVANCE \d3 /  w FoADVANCE \u32ADVANCE \d3)]ADVANCE \u31/2ADVANCE \d3 = 0.059 The standard deviation of an observation of unit weightADVANCE \u34ADVANCE \d3 was 2.92. The weighting scheme was based on counting statistics and included a factor (p = 0.025) to downweight the intense reflections. Plots of  w (|Fo| - |Fc|)ADVANCE \u32ADVANCE \d3 versus |Fo|, reflection order in data collection, sin /, and various classes of indices showed no unusual trends. The maximum and minimum peaks on the final difference Fourier map corresponded to 0.42 and -0.21 eADVANCE \u3-ADVANCE \d3/ADVANCE \u33ADVANCE \d3, respectively. Neutral atom scattering factors were taken from Cromer and WaberADVANCE \u35ADVANCE \d3. Anomalous dispersion effects were included in FcalcADVANCE \u36ADVANCE \d3; the values for f' and f" were those of Creagh and McAuleyADVANCE \u37ADVANCE \d3. The values for the mass attenuation coefficients are those of Creagh and HubbelADVANCE \u38ADVANCE \d3. All calculations were performed using the teXsanADVANCE \u39ADVANCE \d3 crystallographic software package of Molecular Structure Corporation. EXPERIMENTAL DETAILS A. Crystal Data Empirical Formula CADVANCE \d337ADVANCE \u3HADVANCE \d333ADVANCE \u3NADVANCE \d33ADVANCE \u3OADVANCE \d37ADVANCE \u3.CADVANCE \d31.5ADVANCE \u3OADVANCE \d30.5ADVANCE \u3 Formula Weight 657.70 Crystal Color, Habit pale yellow, prism Crystal Dimensions 0.12 X 0.12 X 0.15 mm Crystal System monoclinic Lattice Type Primitive Lattice Parameters a = 8.6682(2) b = 22.6193(5) c = 17.3278(4)  = 96.219(1)ADVANCE \u3oADVANCE \d3 V = 3377.4(1) ADVANCE \u33ADVANCE \d3 Space Group P2ADVANCE \d31ADVANCE \u3/n (#14) Z value 4 DADVANCE \d1calcADVANCE \u1 1.293 g/cmADVANCE \u33ADVANCE \d3 FADVANCE \d1000ADVANCE \u1 1380.00 (MoK) 0.91 cmADVANCE \u3-1ADVANCE \d3 B. Intensity Measurements Diffractometer Nonius KappaCCD Radiation MoK ( = 0.71069 ) graphite monochromated Take-off Angle 2.8ADVANCE \u3oADVANCE \d3 Crystal to Detector Distance 35 mm Temperature -90.0ADVANCE \u3oADVANCE \d3C Scan Rate 60s/frame Scan Width 1.5ADVANCE \u3oADVANCE \d3/frame 2ADVANCE \d1maxADVANCE \u1 55.0ADVANCE \u3oADVANCE \d3 No. of Reflections Measured Total: 7880 Corrections Lorentz-polarization C. Structure Solution and Refinement Structure Solution Direct Methods (SIR92) Refinement Full-matrix least-squares Function Minimized  w (|Fo| - |Fc|)ADVANCE \u32ADVANCE \d3 Least Squares Weights 1/ ADVANCE \u32ADVANCE \d3(Fo) p-factor 0.0250 Anomalous Dispersion All non-hydrogen atoms No. Observations (I>5.00(I)) 4027 No. Variables 619 Reflection/Parameter Ratio 6.51 Residuals: R; Rw 0.048 ; 0.059 Goodness of Fit Indicator 2.92 Max Shift/Error in Final Cycle 0.10 Maximum peak in Final Diff. Map 0.42 eADVANCE \u3-ADVANCE \d3/ADVANCE \u33ADVANCE \d3 Minimum peak in Final Diff. Map -0.21 eADVANCE \u3-ADVANCE \d3/ADVANCE \u33ADVANCE \d3 Table 1. Atomic coordinates and BADVANCE \d1isoADVANCE \u1/BADVANCE \d1eqADVANCE \u1 atom x y z BADVANCE \d1eqADVANCE \u1 O(1) 0.3063(2) 0.34711(8) 0.16700(9) 3.13(5) O(2) -0.2276(2) 0.10552(9) -0.0710(1) 3.98(5) O(3) -0.2825(3) 0.09911(10) 0.0722(1) 5.16(6) O(4) 0.9200(2) 0.16184(7) 0.34442(9) 2.32(4) O(5) 0.7485(2) 0.12267(7) 0.5134(1) 2.78(4) O(6) 1.0317(2) 0.07579(8) 0.5574(1) 3.53(5) O(7) 1.1453(2) 0.13565(8) 0.4775(1) 3.05(4) O(8) 0.278(3) 0.0607(7) 0.1120(7) 9.9(5) O(9) 0.142(2) 0.0681(5) 0.1098(7) 5.4(3) N(1) 0.6707(2) 0.12604(8) 0.3592(1) 2.13(5) N(2) 0.8071(3) 0.25391(9) 0.3336(1) 2.54(5) N(3) 0.1703(3) 0.26060(10) 0.1785(1) 2.93(5) C(1) 0.5567(3) 0.0812(1) 0.3574(1) 2.22(6) C(2) 0.5605(4) 0.0262(1) 0.3934(2) 2.79(7) C(3) 0.4311(3) -0.0093(1) 0.3805(2) 3.09(7) C(4) 0.2986(4) 0.0086(1) 0.3336(2) 3.18(7) C(5) 0.2915(4) 0.0641(1) 0.3006(2) 2.81(7) C(6) 0.4204(3) 0.1015(1) 0.3133(1) 2.26(6) C(7) 0.4484(3) 0.1615(1) 0.2907(1) 2.28(6) C(8) 0.3590(3) 0.2049(1) 0.2491(1) 2.38(6) C(9) 0.4198(3) 0.2603(1) 0.2358(1) 2.31(6) C(10) 0.5733(3) 0.2750(1) 0.2652(1) 2.33(6) C(11) 0.6715(3) 0.3269(1) 0.2660(1) 2.40(6) C(12) 0.6537(4) 0.3833(1) 0.2333(2) 3.22(7) C(13) 0.7768(4) 0.4224(1) 0.2457(2) 4.07(8) C(14) 0.9136(4) 0.4078(1) 0.2907(2) 4.07(8) C(15) 0.9342(4) 0.3527(1) 0.3240(2) 3.35(8) C(16) 0.8127(3) 0.3126(1) 0.3100(1) 2.56(6) C(17) 0.6621(3) 0.2314(1) 0.3077(1) 2.27(6) C(18) 0.6030(3) 0.1747(1) 0.3201(1) 2.16(6) C(19) 0.1946(3) 0.2016(1) 0.2130(2) 2.87(7) C(20) 0.2978(3) 0.2954(1) 0.1907(1) 2.52(6) C(21) 0.0192(4) 0.2805(1) 0.1410(2) 3.42(7) C(22) -0.0524(3) 0.2369(1) 0.0823(1) 3.00(7) C(23) -0.0310(4) 0.2418(1) 0.0047(2) 3.47(8) C(24) -0.0900(4) 0.1987(1) -0.0485(2) 3.62(8) C(25) -0.1708(3) 0.1508(1) -0.0245(1) 3.15(7) C(26) -0.1979(3) 0.1472(1) 0.0540(2) 3.27(7) C(27) -0.1403(3) 0.1896(1) 0.1055(2) 3.27(7) C(28) -0.1715(5) 0.1014(2) -0.1463(2) 5.0(1) C(29) -0.300(1) 0.0921(3) 0.1528(3) 11.6(2) C(30) 0.9202(3) 0.2188(1) 0.3804(1) 2.34(6) C(31) 0.8807(3) 0.2095(1) 0.4639(1) 2.28(6) C(32) 0.8717(3) 0.1416(1) 0.4727(1) 2.20(6) C(33) 0.8387(3) 0.1205(1) 0.3867(1) 2.15(6) C(34) 0.9867(4) 0.2440(1) 0.5238(2) 3.40(8) C(35) 1.0233(3) 0.1137(1) 0.5084(1) 2.48(6) C(36) 1.2949(4) 0.1096(2) 0.5048(2) 3.76(8) C(37) 0.9012(4) 0.0600(1) 0.3695(2) 2.63(7) C(38) 0.413(2) 0.0183(7) 0.019(1) 7.3(5) C(39) 0.290(3) 0.0609(7) 0.0540(9) 4.3(4) C(40) 0.251(1) 0.1003(8) -0.0009(9) 15.2(5) C(41) 0.176(3) 0.0607(7) 0.053(1) 4.1(4) C(42) 0.078(3) 0.0238(8) 0.003(1) 13.1(8) H(1) 0.650(3) 0.015(1) 0.428(1) 2.5(6) H(2) 0.430(3) -0.049(1) 0.406(1) 3.1(6) H(3) 0.207(3) -0.018(1) 0.324(1) 2.8(5) H(4) 0.199(3) 0.079(1) 0.269(1) 2.9(6) H(5) 0.557(4) 0.394(1) 0.200(2) 4.3(7) H(6) 0.767(3) 0.462(1) 0.224(1) 3.8(6) H(7) 1.002(4) 0.436(1) 0.298(2) 5.1(8) H(8) 1.029(3) 0.344(1) 0.357(2) 3.3(6) H(9) 0.128(3) 0.193(1) 0.252(2) 3.4(6) H(10) 0.180(3) 0.170(1) 0.172(1) 2.6(5) H(11) -0.056(3) 0.284(1) 0.186(2) 4.4(6) H(12) 0.037(3) 0.321(1) 0.116(2) 4.7(7) H(13) 0.027(3) 0.276(1) -0.013(1) 4.1(7) H(14) -0.073(3) 0.201(1) -0.105(2) 4.1(6) H(15) -0.158(3) 0.188(1) 0.160(1) 3.0(6) H(16) -0.204(4) 0.060(2) -0.161(2) 5.6(9) H(17) -0.219(4) 0.140(2) -0.180(2) 6.8(9) H(18) -0.046(5) 0.102(1) -0.141(2) 5.9(8) H(19) -0.350(9) 0.120(3) 0.179(5) 17(2) H(20) -0.364(6) 0.063(2) 0.151(3) 9(1) H(21) -0.16(1) 0.091(4) 0.169(5) 22(2) H(22) 1.017(3) 0.2362(9) 0.378(1) 1.0(5) H(23) 0.773(3) 0.2240(9) 0.467(1) 2.0(5) H(24) 0.972(4) 0.284(1) 0.517(2) 5.1(8) H(25) 0.964(4) 0.235(1) 0.578(2) 5.1(7) H(26) 1.102(4) 0.236(1) 0.517(2) 4.6(7) H(27) 1.387(4) 0.133(1) 0.478(2) 6.5(9) H(28) 1.303(3) 0.065(1) 0.488(2) 5.5(8) H(29) 1.310(3) 0.115(1) 0.560(2) 4.5(7) H(30) 0.865(3) 0.047(1) 0.319(2) 4.0(7) H(31) 0.873(3) 0.030(1) 0.405(1) 3.0(6) H(32) 1.018(4) 0.062(1) 0.377(1) 3.5(6) H(33) 0.780(5) 0.127(2) 0.569(2) 8(1) BADVANCE \d1eqADVANCE \u1 = 8/3 ADVANCE \u32ADVANCE \d3(UADVANCE \d111ADVANCE \u1(aa*)ADVANCE \u32ADVANCE \d3 + UADVANCE \d122ADVANCE \u1(bb*)ADVANCE \u32ADVANCE \d3 + UADVANCE \d133ADVANCE \u1(cc*)ADVANCE \u32ADVANCE \d3 + 2UADVANCE \d112ADVANCE \u1(aa*bb*)cos  + 2UADVANCE \d113ADVANCE \u1(aa*cc*)cos  + 2UADVANCE \d123ADVANCE \u1(bb*cc*)cos ) References (X-ray Structure report) 1. SIR92: Altomare, A., Burla, M.C., Camalli, M., Cascarano, M., Giacovazzo, C., Guagliardi, A., Polidori, G.; J. Appl. Cryst., 27, 435-436 (1994). 2. DIRDIF94: Beurskens, P.T., Admiraal, G., Beurskens, G., Bosman, W.P., de Gelder, R., Israel, R. and Smits, J.M.M.(1994). The DIRDIF-94 program system, Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands. 3. Least-Squares: Function minimized Sw(|FADVANCE \d1oADVANCE \u1|-|FADVANCE \d1cADVANCE \u1|)ADVANCE \u32ADVANCE \d3 where w = 4FADVANCE \d1oADVANCE \u1ADVANCE \u32ADVANCE \d3/sADVANCE \u32ADVANCE \d3(FADVANCE \d1oADVANCE \u1ADVANCE \u32ADVANCE \d3) and sADVANCE \u32ADVANCE \d3(FADVANCE \d1oADVANCE \u1ADVANCE \u32ADVANCE \d3) = [SADVANCE \u32ADVANCE \d3(C+RADVANCE \u32ADVANCE \d3B) + (pFADVANCE \d1oADVANCE \u1ADVANCE \u32ADVANCE \d3)ADVANCE \u32ADVANCE \d3]/LpADVANCE \u32ADVANCE \d3 S = Scan rate C = Total integrated peak count R = Ratio of scan time to background counting time B = Total background count Lp = Lorentz-polarization factor p = p-factor 4. Standard deviation of an observation of unit weight: [Sw(|FADVANCE \d1oADVANCE \u1|-|FADVANCE \d1cADVANCE \u1|)ADVANCE \u32ADVANCE \d3/(NADVANCE \d1oADVANCE \u1-NADVANCE \d1vADVANCE \u1)]ADVANCE \u31/2ADVANCE \d3 where NADVANCE \d1oADVANCE \u1 = number of observations and NADVANCE \d1vADVANCE \u1 = number of variables 5. Cromer, D. T. & Waber, J. T.; "International Tables for X-ray Crystallography", Vol. IV, The Kynoch Press, Birmingham, England, Table 2.2 A (1974). 6. Ibers, J. A. & Hamilton, W. C.; Acta Crystallogr., 17, 781 (1964). 7. Creagh, D. C. & McAuley, W.J .; "International Tables for Crystallography", Vol C, (A.J.C. Wilson, ed.), Kluwer Academic Publishers, Boston, Table 4.2.6.8, pages 219-222 (1992). 8. Creagh, D. C. & Hubbell, J.H..; "International Tables for Crystallography", Vol C, (A.J.C. Wilson, ed.), Kluwer Academic Publishers, Boston, Table 4.2.4.3, pages 200-206 (1992). 9. teXsan: Crystal Structure Analysis Package, Molecular Structure Corporation (1985 & 1992) Tamaki et al. 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DE 'r *\C?dnMMArial.er+ 2 UQdnM MArial.erBLCSA (cat.) fR sodnMMArial <L1,2-dichloroethane reflux EAdnMMArialethane refluK14  Z C?dnMMArialethane refluK7 j EAdnMMArialethane refluK15   sodnMMArial <Kmajor single diastereomer- - !mA. CS ChemDraw DrawingChemDraw Interchange FormatChemDraw.Document.4.59q !mA. CS ChemDraw DrawingChemDraw Interchange FormatChemDraw.Document.4.59qObjInfo+CONTENTS@BOlePres000q_1046763332=IE!mA. ^c#^VjCD0100ChemDraw 4.5!Microsoft Word - Supdraf2#2.docc[2  B7 $$$$x s3  `  xg'dd'`Arial  s   @ @s           Z `NH+  3 ڱ      Zy &x  `NH+          ! 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"--$ "---- $-- "-W -- "-W| -- "-# -- "-#W> -- "-|W3 -- "-W>(# -- "-(#( -- "-22 -- "-W( -- "-#8 -- "-Yx -- "-xcs -- "-g} -- "-W>cs -- "-We -- "-e -- "-j -- "- -- "- -- "-x -- "- -- "- -- "-W -- "-WB -- "-^N -- "-csB -- "-eGp -- "-Gp`@ -- "-SpfJ -- "-`@= -- "-=j -- "-Gk -- "-j -- "-' -- "-'7 -- "-7 -- "- -- "- ----$--A7--$876<F8-- "---- $---- $ !--%-- $&'--+!-- $,- --7--$888-- "---- $---- $---- $---- $---- $-- "--//-- $/1/---:!8-- $:<8"6!--!E(A-- $EG A*?)--%P0J-- $P#R$K1I0-- "-/U1J -- "-&1J -- "-T1J -- "-Tx1J -- "-1J -- "-T1J -- "-yT1J -- "-T%1J -- "-%%1J -- "-//1J -- "-T%1J -- "-1J -- "-31J -- "-3`-1J -- "-<d71J -- "-T`-1J -- "-TcY1J -- "-cYV1J -- "-hOL1J -- "-Vv1J -- "-1J -- "-3e1J -- "-e1J -- "-c1J -- "-T1J -- "-T?Y1J -- "-[JZ1J -- "-`-?Y1J -- "-cYD+1J -- "-D+]1J -- "-O*c1J -- "-]1J -- "-%1J -- "-&1J -- "-V%1J -- "-1J -- "-1J -- "-1J -- "-1J -- "-1J ----$----$-- "---- $-- -- $ !--(-- $)*--3--$444-- "---- $---- $---- $~~--vv-- $wuuw--mm-- $nlln--dd-- $ecce-- "---- $---- $--%-- $&%--" ,-- $   !.--- "-,?. -- "-?"]. --:"Arials-.-.:!N:-.-.!N-.-.!O>S-.-.>S!M>S!e>r>!O>"Arials-.G!2G-.>!C>Y-.-.Y!OYY!HY>-.-.>!O>>!B>!n>-.-.!Nz-.-.z!Nz-.-.!O:-.-.:!M:!e:.:C!O:C-.C`!2C`-.:q!C:qU-.-.U!OUU!HU:_-.-.:_!O:_:|!H:| -.-.  !  ! ! )! )4! 4>! >I!HI-.-.-.dd!2d-.-.  !1 !04!%4V! 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ME`eE%b '  t f daOOArial DB[LArialLArial<,L H2 10% Pd-C 6EAdaOOArial Pd-DrArialK18 h  EAdaOOArial Pd-DrArialK20&"DARC-F1CHEMDRAW 4.5MICROSOFT WO010318133400>C   C r  C r C   C  C  N b C 1j C / C  C i N b  C Eb C Vn C T C @ C   C  C j C _ C 9C 9C MO ZC M X? .O # C MC #.C 69OBn H.C ! %)C s "+C &s!# &C 1" $(C &#% C $ N 5c"'6 C Hl&( ,C F' #/C  * 0C j) +3N c*!8 C \c'- C mo, .C k-/ C W. (C )1 C 0 2C l13 C `2 *C (:56<C :489:C .N47&O [68C N75+;X? /5O $5 C N8C :/4=C M:<>O `/=$$$$- -CompObjgjE~ObjInfoGCONTENTSikjOlePres000)RvVjCD0100ChemDraw 4.5!Microsoft Word - Supdraf2#2.doc=lq2  B7 $$$$x s3  `  xg'dd'`Arial HZ 3R 3R H ? ?           MZ  `NM]ZW]019  U 3Ks     K3 Vs MZZ  `NM]W]018     MZs S3 3I D& ! 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