ࡱ> FHE~[ (Gbjbj "xjj1lf f f f f f f  l^4 3VVVVVVVO*Q*Q*Q*@*`-`Q1$4 7Nu1Mf VVVVVu1~"f f VV2~"~"~"V f Vf VO*~"VO*~"~"6&Vy)f f C*V :6 \"+* C* 2037* R7\""R7C*~"z X @f f f f  SUPPORTING INFORMATION FOR: Chemoselective Cross-Metathesis Reaction. Application to the Synthesis of the C1-C14 Fragment of Amphidinol 3 Samir BouzBouz, Janine Cossy Laboratoire de Chimie Organique associ au CNRS, ESPCI,10 rue Vauquelin, 75231 - Paris Cedex 05 - France Experimental Section General considerations: All reactions were carried out under an atmosphere of argon. Solvents, reagents were purified as follows: diethyl ether was distilled over Na/benzophenone, methylene chloride and pyridine were dried by distillation over CaH2. Flash chromatography: Merck silica gel 60 (230-400 mesh), plates eluting with the solvents indicated, visualized by a 254 nm UV lamp, and stained with ethanolic solution of p-anisaldehyde. Nuclear magnetic resonnance spectra were acquired in CDCl3 on a Bruker spectrometer at 300 MHz for 1H and 75 MHz for 13C. Optical rotations were obtained on a Perkin Elmer 241 mc polarimeter (Na d line) using a microcell with a 1 dm path length. Concentration are reported in g/100 mL. Preparation of compound (3)  EMBED ChemDraw.Document.4.5  A flame-dried round-bottomed flask was charged with olefin 1 (0.05 g, 0.51mmol, 1 eq.), acrolein (0.086 g, 1.53 mmol, 3 eq.) and dichloromethane (1 mL). Catalyst I (16 mg, 0.025 mmol, 0.05 eq.) was subsequently added as a solid, producing a light green solution which was stirred for 12 h at rt. The mixture was then concentrated in vacuo to a dark brown oil. Purification of this residue on silica gel by flash chromatography (hexanes/ethyl acetate: 5/5) affords the unstable dialdehyde 3 as a yellow oil (0.055 g, 70%). 1H NMR d: 9.58 (d, J = 7.7 Hz, 1H), 9.51 (d, J = 7.7 Hz, 1H), 6.79 (m, 2H), 6.35 (ddd, J = 1.5, 7.7 and 15.8 Hz, 1H), 6.20 (ddt, J = 1.5, 7.7 and 15.8 Hz, 1H), 4.65 (m, 1H), 3.29 (bs, 1H, OH), 2.70 (m, 2H). Preparation of compound (8)  EMBED ChemDraw.Document.4.5  A flame-dried round-bottomed flask was charged with olefin 6 (0.08 g, 0.057 mmol, 1 eq.), acrolein (0.095 g, 1.71 mmol, 3 eq.) and dichloromethane (3 mL). Catalyst I (18 mg, 0.028 mmol, 0.05 eq.) was subsequently added as a solid, producing a light green solution which was stirred for 12 h at rt. The mixture was then concentrated in vacuo to a dark brown oil. Purification of this residue on silica gel by flash chromatography (hexanes/ethyl acetate: 7/3) affords aldehyde 8 as a yellow oil (0.07 g, 73%). IR(neat): 1740, 1710, 1240 cm-1. 1H NMR d: 9.52 (d, J = 8.1 Hz, 1H), 6.80 (dt, J = 7.0 and 15.8 Hz, 1H), 6.20 (ddt, J = 1.5, 8.1 and 15.6 Hz, 1H), 5.80 (m, 1H), 5.48 (m, 1H), 5.30 (m, 2H), 2.78 (m, 2H), 2.11 (s, 3H). 13C NMR d: 193.3 (s), 169.9 (s), 151.7 (s), 135.3 (d), 134.8 (d), 117.7 (t), 72.2 (d), 37.2 (t), 20.9 (q). Preparation of compound (9)  EMBED ChemDraw.Document.4.5  A flame-dried round-bottomed flask was charged with olefin 7 (0.07 g, 0.324 mmol, 1 eq.), acrolein (0.054 g, 0.972 mmol, 3 eq.) and dichloromethane (3 mL). Catalyst I (10 mg, 0.016 mmol, 0.05 eq.) was subsequently added as a solid, producing a light green solution which was stirred for 12 h at rt. The mixture was then concentrated in vacuo to a dark brown oil. Purification of this residue on silica gel by flash chromatography (hexanes/ethyl acetate: 7/3) affords aldehyde 9 as a yellow oil (0.056 g, 71%). IR(neat): 1740, 1720, 1370, 1240 cm-1. 1H NMR d: 9.53 (d, J = 8.1 Hz, 1H), 7.41-7.22 (m, 5H), 6.81 (dt, J = 7.0 and 15.8 Hz, 1H), 6.67 (d, J = 15.8 Hz, 1H), 6.15 (m, 2H), 5.60 (m, 1H), 2.78 (m, 2H), 2.10 (s, 3H). 13C NMR d: 193.3 (s), 169.9 (s), 151.7 (s), 135.6 (s), 135.3 (d), 133.5 (d), 128.5 (2d, Ar), 128.2 (d), 126.5 (2d, Ar), 125.7 (d), 72.3 (d), 37.6 (t), 21.0 (q). Preparation of compound (11)  EMBED ChemDraw.Document.4.5  A flame-dried round-bottomed flask was charged with olefin 10 (0.25 g, 1.2 mmol, 1 eq.), acrolein (0.2 g, 3.6 mmol, 3 eq.) and dichloromethane (10 mL). Catalyst I (16 mg, 0.03 mmol, 0.025 eq.) was subsequently added as a solid, producing a light green solution which was stirred for 36 h at rt. The mixture was then concentrated in vacuo to a dark brown oil. Purification of this residue on silica gel by flash chromatography (hexanes/ethyl acetate: 7/3) affords compound 11 as a colorless oil (0.212 g, 79%). [a]22D = - 5.2 (c 1, CHCl3). 1H NMR d: 9.48 (d, J = 8.2 Hz, 1H), 6.90 (dt, J = 7.1 and 15.5 Hz, 1H), 6.80 (m, 4H), 6.10 (ddt, J = 1.5, 8.2 and 15.5 Hz, 1H), 4.15 (m, 1H), 3.90 (m, 2H), 3.76 (s, 3H), 3.45 (bs, 1H, OH), 2.60 (m, 2H). 13C NMR d: 194.1 (d), 154.3 (d), 154.0 (s), 152.3 (s), 134.6 (d), 115.5 (2d, Ar), 114.6 (2d, Ar), 72.1 (t), 68.6 (d), 55.5 (q), 36.5 (t). MS m/z 236 (M+, 53), 166 (13), 124 (100), 109 (45). Preparation of compound (12)  EMBED ChemDraw.Document.4.5  Allylmagnesium chloride in THF (0.38 mL of a 2 M solution, 0.762 mmol) was added dropwise over 5 min at 0 C to a solution of (S, S)-II (0.5 g, 0.826 mmol, 1.3 eq.) in ether (10 mL). After stirring for 90 min at 0 C, the slightly orange suspension was cooled at -78 C, and a solution of aldehyde 2 (0.15 g, 0.635 mmol, 1eq.) in ether (3 mL) was added dropwise over a period of 5 min. Stirring at -78 C was continued for 4 h. The reaction mixture was then treated with water (10 mL) stirred for 14 h at 25 C, filtered through Celite and extracted twice with Et2O (2x20 mL) and then with EtOAc (10 mL). The combined organic phases were washed with brine, dried over MgSO4 and concentrated. Purification of the residue on silica gel by flash chromatography (hexanes/ethyl acetate: 7/3) furnished 0.152 g of diol 12 (86% yield). The taddol ligand was recovered (60%). [a]22D = +5 (c 2.3, CHCl3). IR(neat): 3480, 1510, 1230 cm-1. 1H NMR d: 6.80 (m, 4H), 5.90-5.55 (m, 3H), 5.10 (m, 2H), 4.15 (m, 1H), 4.05 (m, 1H), 3.90 (m, 2H), 3.76 (s, 3H), 2.70 (bs, 1H, OH), 2.35 (m, 4H). 2.15 (bs, 1H, OH). 13C NMR d: 154.0 (s), 152.6 (s), 135.7 (d), 134.1 (d), 126.8 (d), 118.0 (t), 115.5 (2d, Ar), 114.6 (2d, Ar), 72.1 (t), 71.3 (d), 69.4 (d), 55.5 (q), 41.7 (t), 36.1 (t). MS m/z 278 (M+, 90), 219 (40), 201 (25), 166 (21), 149 (32), 124 (100), 109 (80), 95 (73). HRMS (CI+) calcd for C16H22O4 278.1518. Found 278.1521. Preparation of compound (13)  EMBED ChemDraw.Document.4.5  Diol 12 (0.1 g, 0.359 mmol) was dissolved in dry pyridine (4 mL), and anhydride acetic (0.5 mL) was added. The mixture was stirred for 12 h at 25 C, quenched with saturated NH4Cl, and extracted with AcOEt. The organic phase was washed with water and then with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified on silica gel by flash chromatography (hexanes/ethyl acetate: 7/3) to afford compound 13 as a yellow oil (0.123 g, 95%). [a]22D = +9 (c 3.9, CHCl3). IR(neat): 1735, 1510 cm-1. 1H NMR d: 6.80 (m, 4H), 5.80-5.50 (m, 3H), 5.30-5.00 (m, 4H), 3.95 (d, J = 4.8 Hz, 2H), 3.75 (s, 3H), 2.50 (m, 2H), 2.35 (m, 2H), 2.05 (s, 3H), 2.00 (s, 3H). 13C NMR d: 170.3 (s), 170.0 (s), 153.9 (s), 152.5 (s), 132.9 (d), 131.6 (d), 127.9 (d), 117.8 (t), 115.5 (2d, Ar), 114.5 (2d, Ar), 73.2 (d), 71.1 (d), 68.7 (t), 55.5 (q), 38.7 (t), 33.5 (t), 21.0 (q), 20.9 (q). MS m/z 362 (M+, 20), 239 (100), 201 (17), 155 (10), 137 (29), 124 (40), 109 (20), 91 (36). HRMS (CI+) calcd for C20H26O6 362.1729. Found 362.1731. Preparation of compound (14)  EMBED ChemDraw.Document.4.5  A flame-dried round-bottomed flask was charged with olefin 13 (0.102 g, 0.281 mmol, 1 eq.), acrolein (0.047 g, 0.845 mmol, 3 eq.) and dichloromethane (3 mL). Catalyst I (9 mg, 0.014 mmol, 0.05 eq.) was subsequently added as a solid, producing a light green solution which was stirred for 12 h at rt. The mixture was then concentrated in vacuo to a dark brown oil. Purification of this residue on silica gel by flash chromatography (hexanes/ethyl acetate: 7/3) affords compound 14 as a yellow oil (0.069 g, 63%). [a]22D = +4 (c 2.6, CHCl3). 1H NMR d: 9.50 (d, J = 7.7 Hz, 1H), 6.83 (m, 4H), 6.71 (dt, J = 7.3 and 15.8 Hz, 1H), 6.13 (ddt, J = 1.5, 7.7 and 15.6 Hz, 1H), 5.75 (m, 1H), 5.54 (m, 1H), 5.35 (m, 1H), 5.20 (m, 1H), 3.95 (d, J = 4.8 Hz, 2H), 3.75 (s, 3H), 2.65 (m, 2H), 2.60-2.40 (m, 2H), 2.05 (s, 3H), 2.00 (s, 3H). 13C NMR d: 193.3 (s), 170.3 (s), 169.8 (s), 154.0 (s), 152.5 (s), 151.7 (d), 135.2 (d), 130.6 (d), 129.2 (d), 115.5 (2d, Ar), 114.5 (2d, Ar), 71.9 (d), 70.9 (d), 68.7 (t), 55.5 (q), 37.4 (t), 33.5 (t), 20.9 (2q). Preparation of compound (15)  EMBED ChemDraw.Document.4.5  Allylmagnesium chloride in THF (0.09 mL of a 2 M solution, 0.178 mmol) was added dropwise over 5 min at 0 C to a solution of (S, S)-II (0.118 g, 0.193 mmol, 1.3 eq.) in ether (5 mL). After stirring for 60 min at 0 C, the slightly orange suspension was cooled at -78 C, and a solution of aldehyde 14 (0.058 g, 0.148 mmol, 1eq.) in ether (3 mL) was added dropwise over a period of 5 min. Stirring at -78 C was continued for 4 h. The reaction mixture was then treated with water (5 mL) stirred for 14 h at 25 C, filtered through Celite and extracted twice with Et2O (2x10 mL) and then with EtOAc (10 mL). The combined organic phases were washed with brine, dried over MgSO4 and concentrated. Purification of the residue on silica gel by flash chromatography (hexanes/ethyl acetate: 7/3) furnished 0.051g of alcohol 15 (80% yield). ([a]22D = +8.2; c 2, CHCl3). IR (neat): 3450, 1740, 1510 cm-1. 1H NMR d: 6.80 (m, 4H), 5.80-5.45 (m, 5H), 5.20-5.10 (m, 4H), 4.10 (m, 1H), 3.95 (d, J = 4.8 Hz, 2H), 3.75 (s, 3H), 2.60-2.20 (m, 7H), 2.10 (s, 3H), 2.00 (s, 3H). 13C NMR d: 170.4 (s), 170.0 (s), 154.0 (s), 152.5 (s), 135.6 (d), 134.0 (d), 131.5 (d), 127.9 (d), 125.5 (d), 117.9 (t), 115.5 (2d, Ar), 114.5 (2d, Ar), 73.4 (d), 71.3 (d), 71.2 (d), 68.8 (t), 55.5 (q), 41.7 (t), 37.0 (t), 33.6 (t), 21.0 (q), 20.9 (q). MS m/z 432 (M+., 9), 309 (48), 267 (11), 201 (34), 171 (33), 137 (27), 124 (100), 105 (64), 91 (64). HRMS (CI+) calcd for C24H32O7 432.2148, Found 432.2149. Preparation of compound (16)  EMBED ChemDraw.Document.4.5  Alcohol 15 (40.5 mg, 0.09mmol) was dissolved in dry pyridine (1 mL) and anhydride acetic (0.1 mL) was added. The mixture was stirred for 12 h at 25 C, quenched with saturated NH4Cl, and extracted with AcOEt. The organic phase was washed with water and then with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel chromatography (hexanes/ethyl acetate: 6/4) to afford compound 16 as a yellow oil (41mg, 92%). [a]22D = +16.1 (c 1.46, CHCl3). IR (neat): 1735, 1510, 1310 cm-1. 1H NMR d: 6.80 (m, 4H), 5.70-5.40 (m, 5H), 5.30-5.00 (m, 5H), 3.95 (d, J = 4.8 Hz, 2H), 3.76 (s, 3H), 2.60-2.30 (m, 6H), 2.10 (s, 3H), 2.05 (s, 3H), 2.00 (s, 3H). 13C NMR d: 170.3 (s), 170.0 (s), 169.9 (s), 154.0 (s), 152.5 (s), 133.0 (d), 131.5 (d), 131.1 (d), 128.2 (d), 128.0 (d), 117.7 (t), 115.6 (2d, Ar), 114.5 (2d, Ar), 73.2 (d), 73.1(d), 71.1 (d), 68.7 (t), 55.6 (q), 38.7 (t), 37.2 (t), 33.5 (t), 21.0 (q), 20.9 (2q). MS m/z 474 (M+, 10), 351 (66), 219 (14), 201 (45), 171 (100), 155 (39), 137 (26), 124 (81), 109 (38), 95 (67). Preparation of compound (17)  EMBED ChemDraw.Document.4.5  A flame-dried round-bottomed flask was charged with olefin 16 (20 mg, 0.04 mmol, 1eq.), ethyl acrylate (12.6 mg, 0.12 mmol, 3 eq.) and dichloromethane (1 mL). Catalyst I (1.3 mg, 0.002 mmol, 0.05 eq.) was subsequently added as a solid, producing a light green solution. After 24 h at 25 C, the mixture was concentrated in vacuo to a dark brown oil. Purification of the residue on silica gel by flash chromatography (hexanes/ethyl acetate: 1/1) affords ester 17 as a yellow oil (14.1 mg, 61%). [a]22D = +4.5 (c 1, CHCl3). IR (neat): 1735, 1720, 1510 cm-1. 1H NMR d: 6.90-6.70 (m, 5H), 5.85 (dt, J = 1.5 and 15.8 Hz, 1H), 5.75-5.10 (m, 7H), 4.15 (q, J = 7.3 Hz, 2H), 3.95 (d, J = 4.8 Hz, 2H), 3.76 (s, 3H), 2.55-2.30 (m, 6H), 2.10 (s, 3H), 2.05 (s, 3H), 2.00 (s, 3H), 1.28 (t, J = 7.3 Hz, 3H). 13C NMR d: 170.3 (s), 169.9 (s), 169.8 (s), 165.9 (s), 154.0 (s), 152.5 (s), 142.8 (d), 131.3 (d), 130.5 (d), 129.0 (d), 128.0 (d), 124.1 (d), 115.5 (2d, Ar), 114.5 (2d, Ar), 73.0 (d), 72.3 (d), 71.1 (d), 68.7 (t), 60.2 (t), 55.7 (q), 37.2 (t), 36.9 (t), 33.5 (t), 21.0 (q), 20.9 (q), 20.8 (q), 14.1 (q). MS m/z 546 (M+, 26), 423 (100), 311 (13), 261 (21), 243 (33), 201 (23), 169 (42), 155 (39), 124 (66), 109 (37), 95 (43). HRMS (CI+) calcd for C29H38O10 546.2465, Found 546.2459. 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