ࡱ>  [rG>wC|e s \ m g [ bjbj^"jj/n4l> > > > & $ P:,f4 >ry:{:{:{:{:{:{:$? Ap:9  :}1> > ;=}1}1}1> 8 y:}1y:}1}1E:v  E: `h ,hE:E:4=0>E:.C..CE:}1 > > > > One-pot direct conversion of 2,3epoxy alcohols into enantiomerically pure 4-hydroxy-4,5dihydroisoxazole 2-oxides Emanuela Marotta, Laure Marie Micheloni, Noemi Scardovi, PaoloRighi* Dipartimento di Chimica Organica A. Mangini Universit di Bologna Viale del Risorgimento, 4 I40136 Bologna (Italy) Email:  HYPERLINK "mailto:righi@ms.fci.unibo.it" righi@ms.fci.unibo.it Supporting Information General: 1H NMR spectra were recorded at 300.00 or 200.00 MHz at 20C with either tetramethylsilane (d 0.00), chloroform (d 7.26), methanol (d 3.30), dimethylsulfoxide (d 2.49) or acetone (d 2.20) as the internal standard. 13C NMR spectra were recorded at 75.46 or 50.3 MHz at 20C with either chloroform (d 77.7) methanol (d 49.3), dimethylsulfoxide (d 39.0) or acetone (d 29.8) as the internal standard. Signal multiplicities were established by DEPT experiments. Melting points were determined through a Bchi instrument and are uncorrected. Specific optical rotations were determined at the sodium D line through a Perkin Elmer 341 polarimeter. Flash chromatographic separations were performed over Merck Silica gel 60 (230-400 mesh), TLC analyses were performed over Merck precoated TLC plates (Silica gel 60 GF254 0.25 mm). Tetrahydrofuran was obtained anhydrous over sodium and benzophenone. Unless otherwise stated, other solvents and reagents were used as received.  EMBED ChemDraw.Document.6.0  General procedure for the one-pot consecutive transformation of 2,3-epoxy alcohols into 4-hydroxy-4,5-dihydroisoxazoles 2-oxides 1. To a stirred solution of 37g of glycidol 3 in dichloromethane (1.1 ml/mmol of 3), TEMPO (0.1 eq) and BAIB (1.1 eq.) were added at room temperature in a round bottomed flask equipped with a CaCl2 tube. The reaction was monitored by TLC and after 4-5h the starting material was consumed. At this point, imidazole (3.3 eq.) and ethyl nitroacetate (1.1 eq.) were added in sequence. The course of the reaction was monitored by TLC and was complete after 18-24 h at room temperature. For water soluble products 1a and 1b the reaction mixture was concentrated in vacuo and purified by flash column chromatography. For products 1c and 1d the reaction mixture was diluted with dichloromethane, washed with a 10% w/w solution of sodium carbonate and with brine; each aqueous layer was back-extracted with dichloromethane. The combined organic layers were dried over magnesium sulfate and concentrated in vacuo and the crude product was purified by flash column chromatography.  EMBED ChemDraw.Document.6.0  (4R,5S)- and (4S,5S)3-Ethoxycarbonyl-4-hydroxy-5-hydroxymethyl-4,5-dihydroisoxazole 2-oxide (1a): flash chromatography (ethyl acetate/petroleum ether = 9/1) afforded 7.98 g of a mixture of the two dihydroisoxazoles (81% yield from 3.55g of 3a). See below for characterization of single isomers.  EMBED ChemDraw.Document.6.0  (4R,5S)- and (4S,5S)-3-Ethoxycarbonyl-4-hydroxy-5-hydroxymethyl-5-methyl-4,5-dihydroisoxazole 2-Oxide (1b): flash chromatography (ethyl acetate/petroleum ether = 7/3) afforded 7.28 g of a mixture of the two dihydroisoxazoles (97% yield from 3.00g of 3b). See below for characterization of single isomers. (4R,5S)- and (4S,5S)-3-Ethoxycarbonyl-4-hydroxy-5-[(S)-hydroxyphenylmethyl]-4,5-dihydroisoxazole 2-Oxide (1c): flash chromatography (ethyl acetate/petroleum ether = 1/1) afforded 6.52g of 4,5cis-1c and 2.79g of 4,5trans-1c (9.31g combined, 71% yield from 7.00g of 3c)  EMBED ChemDraw.Document.6.0  4,5trans-1c: white solid; [a]D24  68.3 (c 0.912; CHCl3); m.p. 118-120C; IR (KBr): n 3395, 3334, 1721, 1625, 1236 cm1; 1H NMR (CD3OD): d 1.29 (t, 3H, J = 7.1 Hz, CH3 (Et)), 4.27 (q, 2H, J = 7.1 Hz, CH2 (Et)), 4.61 (dd, 1H, J = 1.8, 4.4 Hz, C5H), 4.92 (d, 1H, J = 4.4 Hz, C1 H), 5.37 (d, 1H, J = 1.8 Hz, C4H); 13C NMR (CD3OD): d 14.73 (CH3), 62.95 (CH2), 73.39 (CH), 74.13 (CH), 88.93 (CH), 112.80 (C), 127.80 (CH), 129.30 (CH), 129.80 (CH), 140.50 (C), 160.60 (C).  EMBED ChemDraw.Document.6.0  4,5cis-1c: white solid; [a]D26 +10.6 (c 0.995, CHCl3); m.p. 171-173C (decomposition); IR (KBr): n 3515, 3446, 1713, 1599, 1242 cm-1; 1H NMR (CD3OD): d 1.33 (t, 3H, J = 7.1 Hz, CH3 (Et)), 4.31 (q, 2H, J = 7.1 Hz, CH2 (Et)), 6.61 (dd, 1H, J = 5.5, 9.2 Hz, C5H), 5.08 (d, 1H, J = 9.2 Hz, C1 H), 5.41(d, 1H, J = 5.5 Hz, C4H), 7.30-7.46 (m, 5H, arom.);13C NMR (CD3OD): d 14.75 ( CH3), 63.00 (CH2), 70.04 (CH), 73.55 (CH), 84.29 (CH), 114.62 (C), 128.46 (CH), 129.48 (CH), 129.64(CH), 142.42 (C), 160.65 (C). (4R,5R)- and (4S,5R)-5-{(S)-[(2R)-1,4-Dioxaspiro[4.5]dec-2-yl]hydroxymethyl}-3-ethoxycarbonyl-4-hydroxy-4,5-dihydroisoxazole 2-Oxide (1d): flash chromatography (ethyl acetate/petroleum ether = 4/6) afforded 2.72g of 4,5cis1d and 2.26 g of 4,5trans1d (4.98g combined, 62% yield from 4.98g of 3d).  EMBED ChemDraw.Document.6.0  4,5trans-1d: white solid; [a]D27  68.9 (c 1.374; CH3OH); m.p. 142-145C; IR (KBr): n 3479, 3424, 1733, 1612, 1225 cm-1; 1H NMR (CD3OD): d 1.24 (t, 3H, J = 7.1 Hz; CH3 (Et)), 1.34, 1.52 (m, 10H; CH2 (hexyl)), 3.53 (dd, 1H, J = 3.3, 6.6 Hz; C1 H), 3.76 (dd, 1H, J = 7.4, 8.0 Hz; C3  Ha), 3.88 (dd, 1H, J = 6.6, 8.0 Hz; C3  Hb), 4.15 (m, 1H; C2  H), 4.23 (dq, 2H, J = 2.5, 7.1 Hz, CH2 (Et)), 4.36 (dd, 1H, J = 1.6, 6.6 Hz; C5H), 5.49 (d, 1H, J = 1.6 Hz; C4H); 13C NMR (CD3OD): d 15.30 (CH3), 25.66 (CH2), 25.80 (CH2), 27.07 (CH2), 37.47 (CH2), 36.72 (CH2), 63.56 (CH2), 67.04 (CH2), 70.55 (CH), 75.80 (CH), 77.41 (CH), 86.81 (CH), 112.07 (C), 112.97 (C), 161.17 (C).  EMBED ChemDraw.Document.6.0  4,5-cis-1d: white solid; [a]D25  44.3 (c 1.453; CH3OH); m.p. 120-122C; IR (KBr): n 3490, 3456, 1701, 1598, 1244 cm-1; 1H NMR (CD3OD): d 1.23 (t, 3H, J = 7.1 Hz; CH3 (Et)), 1.42, 1.68 (m, 10H; CH2 (hexyl)), 3.90 (dd, 1H, J = 7.1, 7.7 Hz; C3  Ha), 4.04 (dd, 1H, J = 3.0, 9.3 Hz; C1 H), 4.05 (dd, 1H, J = 6.5, 7.7 Hz; C3  Hb), 4.18 (dt, 1H, J = 3.0, 7.1; C2  H), 4.32 (dq, 2H, J = 1.1, 7.1 Hz, CH2 (Et)), 4.55 (dd, 1H, J = 5.5, 9.3 Hz; C5H), 5.36 (d, 1H, J = 5.5 Hz; C4H); 13C NMR (CD3OD): d 15.30 (CH3), 25.70 (CH2), 25.85 (CH2), 27.13 (CH2), 36.67 (CH2), 37.53 (CH2), 63.60 (CH2), 66.75 (CH2), 67.50 (CH), 74.29 (CH), 77.88 (CH), 81.98 (CH), 111.92 (C), 114.75 (C), 161.19 (C).  EMBED ChemDraw.Document.6.0  General procedure of protection of the 4-Hydroxy-4,5-dihydroisoxazole 2-Oxides 1a-b: To a stirred solution of the dihydroisoxazole 1 in dimethylformammide (DMF) (about 1.5 ml/mmol), 2.5 eq of 4dimethylaminopyridine (DMAP) and 2.3 eq of tert-butyldimethylsilylchloride (TDSCl) were added at room temperature in a round-bottomed flask equipped of a calcium chloride tube. After 24 h the reaction was quenched with water (10 ml/mmol of starting material) and the mixture was extracted with ethyl acetate (45 ml/mmol of starting material). The organic layer was dried over sodium sulfate and concentrated in vacuo. The crude product was purified by flash chromatography. (4R,5S)- and (4S,5S)-4-tert-Butyldimethylsiloxy-5-tert-butyldimethylsiloxymethyl-3-ethoxycarbonyl-4,5-dihydroisoxazole 2-Oxide (4a): 8.00 g (39.0 mmol) of starting material 1a afforded 14.63 g of the bisprotected product 4a (86% yield) and 0.75 g of cis-5-monoprotected dihydroisoxazole. Chromatographic conditions: diethyl ether/petroleum ether = 1/9, then 2/8, then 100% ethyl acetate.  EMBED ChemDraw.Document.6.0  4,5trans-4a: white solid; [a]D23  49.2 (c 1.037, CHCl3); m.p. 53-55C; IR (KBr): n 1702, 1735, 1620, 1253 cm-1; 1H NMR (CDCl3): d 0.07 (s, 6H; CH3Si), 0.14 (s, 3H; CH3Si), 0.17 (s, 3H; CH3Si), 0.87 (s, 9H; CH3 (tBu)), 0.90 (s, 9H; CH3 (tBu)), 1.35 (t, 3H, J = 7.1 Hz; CH3 (Et)), 3.70 (dd, 1H, J = 11.1, 5.5 Hz; C1 Ha), 3.80 (dd, 1H, J = 11.1, 3.8 Hz; C1 Hb), 4.26-4.42 (m, 3H; CH2 (Et), C5H), 5.40 (d, 1H, J = 1.2 Hz; C4H); 13C NMR (CDCl3): d -4.57 (CH3), -3.84 (CH3), -3.75 (CH3), 15.32 (CH3), 18.97 (C), 19.16 (C), 26.60 (CH3), 26.72 (CH3), 62.63 (CH2), 62.84 (CH2), 76.92 (CH), 85.04 (CH), 112.00 (C), 159.78 (C).  EMBED ChemDraw.Document.6.0  4,5cis-4a: white solid; [a]D17  33.4 (c 1.036, CHCl3); m.p. 104-107C; IR (KBr): n 1728, 1591, 1232 cm-1; 1H NMR (CDCl3): d 0.05 (s, 9H; CH3Si), 0.15 (s, 3H; CH3Si), 0.85-0.90 (s, 18H; CH3 (tBu)), 1.35 (t, 3H, J = 7.1 Hz; CH3 (Et)), 3.92 (dd, 1H, J = 11.4, 6.8 Hz; C1Ha), 4.10 (dd, 1H, J = 11.4, 5.1 Hz; C1Hb), 4.24 (dq, 1H, J = 11.2, 7.2 Hz; CHa (Et)), 4.28 (dq, 1H, J = 11.2, 7.2 Hz; CHb (Et)), 4.54 (ddd, 1H, J = 6.8, 5.1, 5.2 Hz; C5H), 5.34 (d, 1H, J = 5.2 Hz; C4H); 13C NMR (CDCl3): d  4.93 (CH3),  4.88 (CH3),  4.81 (CH3),  4.72 (CH3), 14.72 (CH3), 18.74 (C), 26.18 (CH3), 26.31 (CH3), 59.84 (CH2), 62.34 (CH2), 73.83 (CH), 82.64 (CH), 112.90 (C), 159.26 (C). (4R,5S)- and (4S,5S)-4-tert-Butyldimethylsiloxy-5-tert-butyldimethylsiloxymethyl-3-etoxycarbonyl-5-methyl-4,5-dihydroisoxazole 2-Oxide (2b): 4.76 g (21.7 mmol) of starting material 1b afforded 8.08 g of the dihydroisoxazoles 4b (83% yield). Chromatographic conditions: diethyl ether/petroleum ether = 5/95, then 1/9.  EMBED ChemDraw.Document.6.0  4,5-trans-4b: white solid; [a]D20  40.3 (c 0.417, CHCl3); m.p. 42-44C; IR (KBr): n 1691, 1611, 1268 cm-1; 1H NMR (CDCl3): d 0.06 (s, 3H; CH3Si), 0.07 (s, 3H; CH3Si), 0.13 (s, 3H; CH3Si), 0.15 (s, 3H; CH3Si), 0.87 (s, 9H; CH3 (tBu)), 0.89 (s, 9H; CH3 (tBu)), 1.35 (t, 3H, J = 7.1 Hz; CH3 (Et)), 1.37 (s, 3H; CH3C5), 3.57 (d, 1H, J = 10.6 Hz; C1 Ha), 3.63 (d, 1H, J = 10.6 Hz; C1 Hb), 4.23 (dq, 1H, J = 10.9, 7.1 Hz; CHa (Et)), 4.42 (dq, 1H, J = 10.9, 7.1 Hz; CHb (Et)), 5.27 (s, 1H, C4H); 13C NMR (CDCl3): d  5.19 (CH3),  4.33 (CH3),  4.15 (CH3), 14.77 (CH3), 15.90 (CH3), 18.53 (C), 18.74 (C), 25.23 (CH3), 62.09 (CH2), 66.89 (CH2), 76.39 (CH), 86.51 (C), 112.90 (C), 159.30 (C).  EMBED ChemDraw.Document.6.0  4,5-cis-4b: white solid; [a]D26 +2.1 (c 0.858, CHCl3); m.p. 82-83C; IR (KBr): n 1729, 1599, 1240 cm-1; 1H NMR (CDCl3): d 0.05 (s, 3H; CH3Si), 0.06 (s, 3H; CH3Si), 0.07 (s, 3H; CH3Si), 0.12 (s, 3H; CH3Si), 0.85 (s, 9H; CH3 (tBu)), 0.88 (s, 9H; CH3 (tBu)), 1.34 (t, 3H, J = 7.1 Hz; CH3 (Et)), 1.38 (s, 3H; CH3C5), 3.78 (d, 1H, J = 11.1 Hz; C1 Ha), 3.92 (d, 1H, J = 11.1 Hz; C1 Hb), 4.24 (dq, 1H, J = 3.9, 7.1 Hz; CHa (Et)), 4.39 (dq, 1H, J = 3.9, 7.1 Hz; CHb (Et)), 5.00 (s, 1H, C4H); 13C NMR (CDCl3): d  5.49 (CH3),  5.12 (CH3),  4.68 (CH3), 14.20 (CH3), 19.20 (C), 19.26 (C), 25.67 (CH3), 61.73 (CH2), 63.57 (CH2), 78.70 (CH), 86.30 (C), 112.10 (C), 159.00 (C).  EMBED ChemDraw.Document.6.0  General procedure of deoxygenation of the dihydroisoxazoles 4a-b: The starting material was dissolved in 4 ml/mmol of trimethyl phosphite in a flask equipped with a condenser and a termometer. The mixture was stirred at 100C for 5 h, then diethyl ether was added (25 ml/mmol of starting material) and the solution was washed with HCl 1N (310 ml/mmol of starting material), water (10 ml/mmol) and brine (5 ml/mmol). The organic layer was dried over sodium sulfate and concentrated in vacuo to give a crude product which could be used without further purification.  EMBED ChemDraw.Document.6.0  (4R,5S)-4-tert-Butyldimethylsiloxy-5-tert-butyldimethylsiloxymethyl-3-ethoxycarbonyl-4,5-dihydroisoxazole (4,5trans-5a): 0.30 g (0.7 mmol) of the starting material trans-4a afforded 0.29 g of the product trans-5a (quantitative yield): colourless oil; [a]D26  72.1 (c 0.957, CHCl3); 1H NMR (CDCl3): d 0.02 (s, 3H; CH3Si), 0.03 (s, 3H; CH3Si), 0.11 (s, 3H; CH3Si), 0.13 (s, 3H; CH3Si), 0.83 (s, 9H; CH3 (tBu)), 0.84 (s, 9H; CH3 (tBu)), 1.33 (t, 3H, J = 7.1 Hz; CH3 (Et)), 3.53 (dd, 1H, J = 11.0, 6.2 Hz; C1 Ha), 3.76 (dd, 1H, J = 11.0, 4.0 Hz; C1 Hb), 4.32 (q, 1H, J = 7.1 Hz; CHa (Et)), 4.33 (q, 1H, J = 7.1 Hz; CHb (Et)), 4.46 (ddd, 1H, J = 6.2, 4.0, 2.6 Hz; C5H), 5.25 (d, 1H, J = 2.6 Hz; C4H); 13C NMR (CDCl3): d  5.49 (CH3),  4.93 (CH3),  4.82 (CH3), 14.19 (CH3), 17.97 (C), 18.22 (C), 25.70 (CH3), 25.79 (CH3), 61.44 (CH2), 61.85 (CH2), 77.36 (CH), 90.83 (CH), 152.71 (C), 160.21 (C).  EMBED ChemDraw.Document.6.0  (4S,5S)-4-tert-Butyldimethylsiloxy-5-tert-butyldimethylsiloxymethyl-3-ethoxycarbonyl-4,5-dihydroisoxazole (4,5cis-5a): 1.00 g (2.3 mmol) of the starting material cis-4a afforded 0.96 g of the product cis-5a (quantitative yield): colourless oil; [a]D25  59.5 (c 0.964, CHCl3); 1H NMR (CDCl3): d 0.10-0.14 (s, 9H; CH3Si), 0.15 (s, 3H; CH3Si), 0.85 (s, 9H; CH3 (tBu)), 0.90 (s, 9H; CH3 (tBu)), 1.40 (t, 3H, J = 7.1 Hz; CH3 (Et)), 3.95 (dd, 1H, J = 11.3, 6.9 Hz; C1 Ha), 4.06 (dd, 1H, J = 11.3, 5.2 Hz; C1 Hb), 4.30-4.35 (m, 1H; C5H), 4.31 (dq, 1H, J = 10.8, 7.1 Hz; CHa (Et)), 4.41 (dq, 1H, J = 10.8, 7.1 Hz; CHb (Et)), 5.21 (d, 1H, J = 6.7 Hz; C4H); 13C NMR (CDCl3): d  4.92 (CH3),  4.30 (CH3),  4.25 (CH3),  4.13 (CH3), 15.19 (CH3), 19.24 (C), 19.40 (C), 26.69 (CH3), 26.92 (CH3), 60.36 (CH2), 63.05 (CH2), 75.17 (CH), 89.05 (CH), 154.87 (C), 161.41 (C).  EMBED ChemDraw.Document.6.0  (4R,5S)-4-tert-Butyldimethylsiloxy-5-tert-butyldimethylsiloxymethyl-3-ethoxycarbonyl-5-methyl-4,5-dihydroisoxazole (trans-5b): 0.32 g (0.7 mmol) of the starting material trans-4b afforded 0.29 g of the product trans-5b (quantitative yield): colourless oil; [a]D28  48.1 (c 1.247, CHCl3); 1H NMR (CDCl3): d 0.02 (s, 3H; CH3Si), 0.03 (s, 3H; CH3Si), 0.12 (s, 3H; CH3Si), 0.13 (s, 3H; CH3Si), 0.85 (s, 18H; CH3 (tBu)), 1.34 (t, 3H, J = 7.1 Hz; CH3 (Et)), 1.35 (s, 3H; CH3C5), 3.34 (d, 1H, J = 10.2 Hz; C1 Ha), 3.52 (d, 1H, J = 10.2 Hz; C1 Hb), 4.27 (dq, 1H, J = 10.7, 7.1 Hz; CHa (Et)), 4.37 (dq, 1H, J = 10.7, 7.1 Hz; CHb (Et)), 5.10 (s,1H, C4H); 13C NMR (CDCl3): d  5.60 (CH3),  5.50 (CH3),  5.02 (CH3),  4.66 (CH3), 14.20 (CH3), 15.34 (CH3), 18.20 (C), 25.69 (CH3), 25.77 (CH3), 61.75 (CH2), 65.86 (CH2), 76.84 (CH), 92.39 (C), 153.10 (C), 160.70 (C).  EMBED ChemDraw.Document.6.0  (4S,5S)-4-tert-Butyldimethylsiloxy-5-tert-butyldimethylsiloxymethyl-3-ethoxycarbonyl-5-methyl-4,5-dihydroisoxazole (4,5-cis-5b): 1.43 g (3.2 mmol) of the starting material cis-4b afforded 1.35 g of product cis-5b (95% yield) after flash chromatography (diethyl ether/petroleum ether = 1/9): white solid; [a]D27  8.4 (c 0.834, CHCl3); m.p. 58-60C; IR (KBr): n 1721, 1579 cm-1; 1H NMR (CDCl3): d 0.08 (s, 3H; CH3Si), 0.10 (s, 3H; CH3Si), 0.12 (s, 3H; CH3Si), 0.14 (s, 3H; CH3Si), 0.86 (s, 9H; CH3 (tBu)), 0.92 (s, 9H; CH3 (tBu)), 1.28 (s, 3H; CH3C5), 1.38 (t, 3H, J = 7.1 Hz; CH3 (Et)), 3.83 (d, 1H, J = 11.0 Hz; C1 Ha), 3.88 (d, 1H, J = 11.0 Hz; C1 Hb), 4.30 (dq, 1H, J = 10.7, 7.1 Hz; CHa (Et)), 4.40 (dq, 1H, J = 10.7, 7.1 Hz; CHb (Et)), 4.78 (s,1H, C4H); 13C NMR (CDCl3): d  4.29 (CH3),  3.88 (CH3), 15.20 (CH3), 19.20 (C), 19.45 (C), 20.48 (CH3), 26.70 (CH3), 26.98 (CH3), 62.94 (CH2), 64.22 (CH2), 81.06 (CH), 92.96 (C), 153.90 (C), 161.76 (C).  EMBED ChemDraw.Document.6.0  General procedure of desilylation: To a stirred solution of the dihydroisoxazole in anhydrous tetrahydrofuran (THF) (3 ml/mmol), 2.8 eq of tetrabutylammoniumfluoride (1M in THF) were added at room temperature in a round-bottomed flask equipped of a calcium chloride tube. After 5 minutes the TLC analisys (ethyl acetate) revealed that the starting material was consumed, ethanol was added (6 ml/mmol), the mixture was stirred for 1 h and concentrated in vacuo. The crude product was purified by flash chromatography.  EMBED ChemDraw.Document.6.0  (4R,5S)-3-Ethoxycarbonyl-4-hydroxy-5-hydroxymethyl-4,5-dihydroisoxazole 2-Oxide (4,5-trans-1a): 0.350 g (0.71 mmol) of the starting material trans-4a afforded 0.115 g (78% yield) of the deprotected dihydroisoxazole trans-1a; chromatographic conditions: ethyl acetate/petroleum ether = 1/1 then 8/2: colourless oil; [a]D24  95.8 (c 0.711, EtOH); 1H NMR ((CD3)2CO): d 1.29 (t, 3H, J = 7.0 Hz; CH3 (Et)), 3.80 (d, 2H, J = 4.4 Hz; C1 H2), 4.27 (q, 1H, J = 7.0 Hz; CHa (Et)), 4.28 (q, 1H, J = 7.0 Hz; CHb (Et)), 4.53 (dd, 1H, J = 4.4, 2.2 Hz; C5H), 5.42 (d, 1H, J = 2.2 Hz; C4H); 13C NMR ((CD3)2CO): d 14.82 (CH3), 62.22 (CH2), 75.34 (CH), 85.82 (CH), 112.19 (C), 159.79 (C).  EMBED ChemDraw.Document.6.0  (4S,5S)-3-Ethoxycarbonyl-4-hydroxy-5-hydroxymethyl-4,5-dihydroisoxazole 2-Oxide (4,5-cis-1a): 0.140 g (0.28 mmol) of the starting material cis-4a afforded 0.053 g (91% yield) of the deprotected dihydroisoxazole cis-1a; chromatographic conditions: ethyl acetate: clourless oil; [a]D25  42.6 (c 0.393, EtOH); 1H NMR ((CD3)2CO): d 1.29 (t, 3H, J = 7.1 Hz; CH3 (Et)), 3.98 (dd, 1H, J = 12.3, 6.6 Hz; C1 Ha), 4.07 (dd, 1H, J = 12.3, 4.4 Hz; C1 Hb), 4.27 (q, 1H, J = 7.1 Hz; CHa (Et)), 4.28 (q, 1H, J = 7.1 Hz; CHb (Et)), 4.78 (ddd, 1H, J = 6.6, 4.4, 6.1 Hz; C5H), 5.50 (d, 1H, J = 6.1 Hz; C4H); 13C NMR ((CD3)2CO): d 14.41 (CH3), 59.33 (CH2), 61.70 (CH2), 73.39 (CH), 82.17 (CH), 112.71 (C), 159.28 (C).  EMBED ChemDraw.Document.6.0  (4R,5S)-3-Ethoxycarbonyl-4-hydroxy-5-hydroxymethyl-5-methyl-4,5-dihydroisoxazole 2-Oxide (4,5-trans-1b): 0.340 g (0.70 mmol) of the starting material trans-4b afforded 0.130 g (88% yield) of the deprotected dihydroisoxazole trans-1b; chromatographic conditions: ethyl acetate/petroleum ether = 8/2: white solid; [a]D27  56.6 (c 1.085, EtOH); IR (KBr): n 3433, 3333, 1728, 1616, 1249 cm-1; 1H NMR ((CD3)2CO): d 1.29 (t, 3H, J = 7.1 Hz; CH3 (Et)), 1.41 (s, 3H; CH3C5), 3.62 (d, 1H, J = 11.8 Hz; C1 Ha), 3.67 (d, 1H, J = 11.8 Hz; C1 Hb), 4.26 (q, 2H, J = 7.1 Hz; CH2 (Et)), 5.27 (s, 1H, C4H); 13C NMR ((CD3)2CO): d 15.45 (CH3), 15.96 (CH3), 62.67 (CH2), 67.38 (CH2), 76.26 (CH), 87.92 (C), 113.88 (C), 160.59 (C).  EMBED ChemDraw.Document.6.0  (4S,5S)-3-Ethoxycarbonyl-4-hydroxy-5-hydroxymethyl-5-methyl-4,5-dihydroisoxazole 2-Oxide (4,5-cis-1b): 0.19 g (0.4 mmol) of the starting material cis-4b afforded 0.07 g (85% yield) of the deprotected dihydroisoxazole cis-1b; chromatographic conditions: ethyl acetate: colourless oil; [a]D25 +18.5 (c 0.546, CHCl3); 1H NMR (CD3OD): d 1.33 (t, 3H, J = 7.1 Hz, CH3 (Et)), 1.43 (s, 3H, CH3), 3.81 (d, 1H, J = 12.1 Hz, C1 Ha), 3.88 81 (d, 1H, J = 12.1 Hz, C1 Hb), ), 4.31 (q, 2H, J = 7.1 Hz, CH2 (Et)), 5.06 (s, 1H, C4H); 13C NMR (CD3OD): d 14.71 (CH3), 20.23 (CH3), 62.94 (CH2), 63.59 (CH2), 79.04 (CH), 87.03 (C), 113.53 (C), 160.82 (C).  EMBED ChemDraw.Document.6.0   EMBED ChemDraw.Document.6.0  (4R,5S)-3-Ethoxycarbonyl-4-hydroxy-5-hydroxymethyl-4,5-dihydroisoxazole (4,5trans-9a): 0.30 g (0.7 mmol) of the starting material trans-5a afforded 0.10 g (83% yield) of the free dihydroisoxazole 4,5-trans-9a; chromatographic conditions: ethyl acetate/petroleum ether = 8/2: colourless oil; [a]D22  112.3 (c 0.768, EtOH); 1H NMR ((CD3)2CO): d 1.32 (t, 3H, J = 7.1 Hz; CH3 (Et)), 3.67 (dd, 1H, J = 12.1, 4.9 Hz; C1 Ha), 3.74 (dd, 1H, J = 12.1, 4.9 Hz; C1 Hb), 4.31 (q, 1H, J = 7.1 Hz; CHa (Et)), 4.32 (q, 1H, J = 7.1 Hz; CHb (Et)), 4.54 (dt, 1H, J = 4.9, 3.6 Hz; C5H), 5.31 (d, 1H, J = 3.6 Hz; C4H); 13C NMR ((CD3)2CO): d 15.35 (CH3), 62.64 (CH2), 63.08 (CH2), 77.93 (CH), 93.06 (CH), 155.24 (C), 161.98 (C).  EMBED ChemDraw.Document.6.0  (4S,5S)-3-Ethoxycarbonyl-4-hydroxy-5-hydroxymethyl-4,5-dihydroisoxazole (4,5-cis-9a): 0.25 g (0.6 mmol) of the starting material cis-5a afforded 0.07 g (70% yield) of the dihydroisoxazole cis-9a; chromatographic conditions: ethyl acetate/petroleum ether = 8/2: semisolid; [a]D28  107.2 (c 0.622, EtOH); IR (KBr): n 3388, 1729, 1587 cm-1; 1H NMR ((CD3)2CO): d 1.82 (t, 3H, J = 7.0 Hz; CH3 (Et)), 3.89-4.19 (m, 3H; C1 H2, C1 OH), 4.31 (q, 2H, J = 7.0 Hz; CH2 (Et)), 4.53 (m, 1H; C5H), 5.17 (d, 1H, J = 6.0 Hz; C4OH), 5.38 (dd, 1H, J = 6.0 Hz; C4H); 13C NMR ((CD3)2CO): d 15.37 (CH3), 60.11 (CH2), 63.03 (CH2), 75.72 (CH), 88.79 (CH), 155.95 (C), 161.95 (C).  EMBED ChemDraw.Document.6.0  (4R,5S)-3-Ethoxycarbonyl-4-hydroxy-5-hydroxymethyl-5-methyl-4,5-dihydroisoxazole (4,5-trans-9b): 0.26 g (0.5 mmol) of the starting material trans-5b afforded 0.10 g (92% yield) of the dihydroisoxazole trans-9b chromatographic conditions: ethyl acetate/petroleum ether = 8/2: colourless oil; [a]D28  70.4 (c 1.034, EtOH); 1H NMR ((CD3)2CO): d 1.31 (t, 3H, J = 7.1 Hz; CH3 (Et)), 1.38 (s, 3H; CH3C5), 3.43 (d, 1H, J = 11.4 Hz; C1 Ha), 3.55 (d, 1H, J = 11.4 Hz; C1 Hb), 4.29 (q, 1H, J = 7.1 Hz; CHa (Et)), 4.30 (q, 1H, J = 7.1 Hz; CHb (Et)), 5.13 (s, 1H; C4H); 13C NMR ((CD3)2CO): d 15.40 (CH3), 15.79 (CH3), 62.94 (CH2), 67.12 (CH2), 77.50 (CH), 94.09 (C), 155.35 (C), 162.26 (C).  EMBED ChemDraw.Document.6.0  (4S,5S)-3-Ethoxycarbonyl-4-hydroxy-5-hydroxymethyl-5-methyl-4,5-dihydroisoxazole (4,5-cis-9b): 0.40 g (0.8 mmol) of the starting material cis-5b afforded 0.10 g (60% yield) of the dihydroisoxazole cis-9b; chromatographic conditions: ethyl acetate/diethyl ether = 1/9: colourless oil: [a]D25 +4.1 (c 0.888, CHCl3); 1H NMR (CDCl3): d 1.31 (s, 3H; CH3C5), 1.33 (t, 3H, J = 7.1 Hz; CH3 (Et)), 3.38 (bs, 1H; C1 OH), 3.90 (bs, 2H; C1 H2), 4.32 (q, 2H, J = 7.1 Hz; CH2 (Et)), 4.51 (d, 1H, J = 4.7 Hz; C4OH), 5.00 (d, 1H, J = 4.7 Hz, C4H); 13C NMR (CDCl3): d 13.86 (CH3), 20.58 (CH3), 62.12 (CH2), 63.77 (CH2), 80.60 (CH), 90.56 (C), 152.56 (C), 160.46 (C).  EMBED ChemDraw.Document.6.0  (4R,5S)-3-Ethoxycarbonyl-4-hydroxy-5-[(S)-hydroxyphenylmethyl]-4,5-dihydroisoxazole (4,5-trans-9c): 0.17 g (0.3 mmol) of the starting material trans-5c afforded 0.06 g (76% yield) of the dihydroisoxazole trans-9c; chromatographic conditions: diethyl ether/petroleum ether = 1/1: semisolid; [a]D24  112.9 (c 0.328, CHCl3); IR (NaCl): n 3419, 1717, 1590 cm-1; 1H NMR (DMSO-d6): d 0.84 (t, 3H, J = 7.1 Hz; CH3 (Et)), 3.84 (q, 2H, J = 7.1 Hz; CH2 (Et)), 4.10 (dd, 1H, J = 5.2, 3.3 Hz; C5H), 4.27 (bd, 1H; C4H), 4.74 (bs, 1H; C1 H), 5.45 (bs, 1H; C1 OH), 5.70 (bd, 1H, C4OH), 6.86-7.25 (m, 5H; arom.); 13C NMR (DMSO-d6): d 13.96 (CH3), 61.34 (CH2), 70.76 (CH), 74.26 (CH), 93.95 (CH), 126.58 (CH), 127.38 (CH), 128.14 (CH), 140.74 (C), 153.38 (C), 159.86 (C).  EMBED ChemDraw.Document.6.0  (4S,5S)-3-Ethoxycarbonyl-4-hydroxy-5-[(S)-hydroxyphenylmethyl]-4,5-dihydroisoxazole (4,5-cis-9c): 0.08 g (0.15 mmol) of the starting material cis-5c afforded 0.05 g (quant. yield) of the dihydroisoxazole cis-9c; chromatographic conditions: ethyl acetate/petroleum ether = 1/1: white solid; [a]D25  44.5 (c 1.56, CHCl3); m.p. 151-153C; IR (KBr): n 3521, 3431, 1727, 1589; 1H NMR (DMSO-d6): d 1.30 (t, 3H, J = 7.1 Hz; CH3 (Et)), 4.28 (q, 2H, J = 7.1 Hz; CH2 (Et)), 4.29 (dd, 1H, J = 9.4, 6.8 Hz; C5H), 4.90 (dd, 1H, J = 9.4, 4.7 Hz; C1 H), 5.14 (dd, 1H, J = 7.5, 6.8 Hz; C4H), 5.68 (d, 1H, J = 4.7 Hz; C1 OH), 6.18 (d, 1H, J = 7.5 Hz; C4OH), 7.20-7.50 (m, 5H; arom.); 13C NMR (DMSO-d6): d 13.97 (CH3), 61.30 (CH2), 67.68 (CH), 72.54 (CH), 88.68 (CH), 127.26 (CH), 127.49 (CH), 127.96 (CH), 142.44 (C), 155.23 (C), 159.89 (C).  EMBED ChemDraw.Document.6.0  (4S,5S)-4-tert-Butyldimethyldimethylsilyloxy-3,5-bis(tert-butyldimethylsilyloxymethyl)-5-methyl-4,5-dihydroisoxazole (6). Sodium borohydride (660 mg, 17.4 mmol) was added to a flame-dried three-neck flask containing 4,5-cis-5b (5.00 g, 11.6 mmol) and EtOH (24 ml) at 10C. The reaction mixture was allowed to reach room temperature and was stirred until TLC showed that there was no more starting material (ca.16 h). Excess borohydride was destroyed with 1 N hydrochloric acid and the mixture was diluted with water (50 ml). The aqueous layer was extracted with EtOAc (5 x 25 ml) and the combined organic layers were washed with brine (15 ml) and dried over magnesium sulphate. The solvent was removed by rotary evaporation to afford 4.30 g (95 % yield) of a colourless liquid which crystallized after ca.1 h and was used without further purification. 1H NMR (CDCl3): ( 0.08 (s, 6H), 0.12 (s, 3H), 0.16 (s, 3H), 0.90 (s, 18H), 1.29 (s, 3H), 3.05 (bs, 1H), 3.72 (d, J =11.0 Hz, 1H), 3.78 (d, J =11.0 Hz, 1H), 4.28 (d, J =14.0 Hz, 1H), 4.46 (d, J =14.0 Hz, 1H), 4.80 (s, 1H); 13CNMR (CDCl3): ( -4.92; -4.86; -4.55; -4.35 (CH3Si), 18.45; 18.91 (C), 20.60 (CH3), 26.06; 26.43 (CH3) 56.40 (CH2), 64.18 (CH2), 82.01 (CH), 88.33 (C), 159.81 (C); mp 44-46C ; [(]D22 +28.2 (c 1.02; CH3Cl) To a stirred solution of crude alcohol (4.3 g, 11.0 mmol) in DMF (20 ml) DMAP (4.3 mg, 35.2 mmol), and tert-butyldimethylsilyl chloride (2.58 g, 17.1 mmol) were added. The mixture was kept stirring at room temperature for 22 h, and then it was partitioned between water and ethyl acetate. The aqueous layer was extracted 3 times with EtOAc. The crude product was purified by column chromatography (petroleum ether- Et2O, 9:1) to give 6 (4.90 g, 86% yield) as a white solid. mp 41-43C; [(]D22 -6.30 (c 1.007; CH3Cl); 1H NMR (CDCl3): ( 0.07-0.16 (m, 18H), 0.90 (s, 27 H ), 1.30 (s, 3H), 3.80(s, 2H), 4.35(d, J =12.7 Hz,1H), 4.40(d, J =12.7 Hz,1H), 4.72 (s, 1H); ); 13C NMR (CDCl3): ( -4.35; -4.31; -4.27; -4.13; -4.06; -3.81 (CH3Si), 19.10; 19.50 (C), 21.23 (CH3); 26.70; 26.79; 27.04 (CH3), 57.30 (CH2),64.70(CH2), 82.10 (CH), 88.45 (C), 160.00 (C).  EMBED ChemDraw.Document.6.0  (2R,3S,4R)-2-Acetamido-4-methyl-1,3,5-triacetoxy-pentan-4-ol (8): 1.20 g (2.0 mmol) of 6 was dissolved in 2.5 ml of anhydrous diethyl ether, 5.3 ml (5.3 mmol) of a 1M solution of lithium aliuminum hydride in diethyl ether were added dropwise at 10C. After 4h at 0C the TLC analysis (petroleum ether/diethyl ether = 9/1) revealed that the starting material was consumed. 5.0 ml of HCl 6N were then added dropwise at 5C and the mixture was extracted several times with ethyl acetate, the organic layer was washed with 30 ml of brine, dried with magnesium sulfate and concentrated in vacuo. The residual was dissolved in 4.0 ml of a 3 : 1 mixture of methanol/tetrahydrofuran, 2 ml of HCl 6N were added and the mixture was rifluxed for 3h. Concentration under reduced pressure afforded 560 mg (82% yield) of a brown oil constituted by the wished product which was characterized through the subsequent derivatization. The crude product of the previous reaction was dissolved in 3 ml of dry pyridine under nitrogen. 0.92 ml (9.8 mmol) of acetic anhydride were added dropwise at room temperature. After 20 h the mixture was concentrated in vacuo, dissolved in 5 ml of chloroform and washed with 3 ml of a saturated solution of sodium carbonate, with 5 ml of a saturated solution of copper sulfate and with 10 ml of brine. Each aqueous layer was back-extracted with chloroform, the reunited organic layer was dried with magnesium sulfate and concentrated in vacuo to give 430 mg (78% yield, 64% overall) of a yellow oil constituted by the mixture (d.e. > 9:1 by 1H NMR) of the two tetraacetilated isomers. [(]18D25.2 (c 1.622, CHCl3). 1H NMR (CDCl3): d 1.30 (s, 3H, CH3), 1.94 (s, 3H, CH3 (Ac)), 1.99 (s, 3H, CH3 (Ac)), 2.01 (s, 3H, CH3 (Ac)), 2.07 (s, 3H, CH3 (Ac)), 3.50 (bs, 1H, OH), 3.92 (d, 1H, J = 11.4 Hz, C5Ha), 4.04 (dd, 1H, J = 4.6, 11.3 Hz, C1Ha), 4.08 (d, 1H, J = 11.4 Hz, C5Hb), 4.10 (dd, 1H, J = 6.4, 11.3 Hz, C1Hb), 4.65 (m, 1H, C2H), 5.04 (d, 1H, J = 2.2, C3H), 6.40 (d, 1H, J = 8.4 Hz, NH); 13C NMR (CDCl3): d 21.13 (CH3), 21.18 (CH3), 21.26 (CH3), 22.32 (CH3), 23.53 (CH3), 47.75 (CH), 64.27 (CH2), 68.37 (CH2), 73.30 (C), 73.44 (CH), 170.60 (C), 171.29 (C), 171.30 (C).  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" # $ % & ' ( ) * + , - . / 0 1 2 3 4 5 6 7 8 b ; < = > ? @ A B C D E F G H I J K L M N O P Q R S T U V W X Y Z [ \ ] ^ _ ` a d g h i j k l m n o p q r s t u v w x y z { | } ~  `''@,#Arial,Arial,Arial,Arial,Arial, Arial, Arial,Arial,Arial,Arial,Arial,Arial,Arial,Arial, ^   CCQEuC@DECCCQECCCQECAFT 4,5-trans-4b} &CuCDCXCC&CuCDuC&CuCDuCAFT}Acquisition Time (sec)m VDuCVDCVuDCVDuCVDuCVDuCVDuCAFTe3.6405n 7DuC剋DCsgDC7DuC剋DuC7DuC剋DuCAFT}Commentk ɓEuCc0EC{$ECɓEuCc0EuCɓEuCc0EuCAFT}Daten s^/EuCs~6ECs2ECs^/EuCs~6EuCs^/EuCs~6EuCAFTr1-04-00v &CCDCUCC&CCDC&CCDCAFT}Frequency (MHz)m VDCVDCVuDCVDCVDCVDCVDCAFTe300.08n 7DC剋DCsgDC7DC剋DC7DC剋DCAFT}Nucleusi :DC:DC:?DC:DC:DC:DC:DCAFT,1H{ sDCsDCsκDCsDCsDCsDCsDCAFT}Number of Transientsi ɓDCSDCDCɓDCSDCɓDCSDCAFT&16| DC ECECDC ECDC ECAFT}Original Points Countl , EC,EC,EC, EC,EC, EC,ECAFT\12000s ɓECc0EC{$ECɓECc0ECɓECc0ECAFT} Points Countl s^/ECs5ECs>2ECs^/ECs5ECs^/ECs5ECAFT\16384n &CCDCXCC&CCDC&CCDCAFT}Solventl VDCVDCVDCVDCVDCVDCVDCAFTOcdcl3w 7DC剋DCsgDC7DC剋DC7DC剋DCAFT}Sweep Width (Hz)n :DC:_DC:DC:DC:_DC:DC:_DCAFTw4500.45{ sDCsDCsκDCsDCsDCsDCsDCAFT}Temperature (grad C)m ɓDC3DCDCɓDC3DC3DCɓDCAFTe20.0000CuC3DuC3DCCC03DuCEuCEC3DC0EuCQEuCQECEC0CC3DC3DCCC03DCDCDC3DC0DCDCDCDC0DCECECDC0ECQECQECEC0CC3DC3DCCC03DCDCDC3DC0DCDCDCDC#?1!PCrxD!#?2`CmD!#?3jCbD!#?48 CxD!#?56/CmdD!#?6)fCwrD!#?7[C|D!#?8UCD\D!#?90|CxD!$?10C{D!$? 11/4CD!$?12@CϩD!$?13PDCD!$?14KC͘D!$?15LC{@D!$?16ҚCID!$? 17{D)D!$?18 DD!$?19VDÐD!$?20C܁D!$?21DnD!$?22. 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G~?e?NOS?lq???F?$3?T$CompObjoObjInfoOle10Nativet `NOle10ItemName eFACD ChemSketch 2.0ACD.ChemSketch.20ACD.ChemSketch.209q1 eFACD.ChemSketch.20ACD.ChemSketch.20ACD.ChemSketch.209q / Z \N''A9A9 N, Arial,Arial,Arial,Arial, Arial, Arial,Arial,Arial,Arial,Arial,Arial,Arial,Arial, ^   CCQEuC@DECCCQECCCQECAFT 4,5-trans-5a} &CuCDCXCC&CuCDuC&CuCDuCAFT}Acquisition Time (sec)m VDuCVDCVuDCVDuCVDuCVDuCVDuCAFTe0.5464n ^,DuC]υDC[DC^,DuC]υDuC^,DuC]υDuCAFT}Commentk jDuCAECjDCjDuCAEuCjDuCAEuCAFT}Daten `<EuC`\ EC`EC`<EuC`\ EuC`<EuC`\ EuCAFTr1-26-00v  EuC$ECEC EuC$EuC EuC$EuCAFT}Frequency (MHz)l c#EuCc)ECc&ECc#EuCc)EuCc#EuCc)EuCAFTS50.29n -EuCEEC9EC-EuCEEuC-EuCEEuCAFT}Nucleusj gDEuCgvHECgFECgDEuCgvHEuCgvHEuCgDEuCAFT>13C| &CCDCUCC&CCDC&CCDCAFT}Original Points Countk VDCVUDCVDCVDCVUDCVUDCVDCAFTJ8000s ^,DC]υDC[DC^,DC]υDC^,DC]υDCAFT} Points Countk ăDCDCdDCăDCDCDCăDCAFTJ8192n cDCc)DCcYDCcDCc)DCcDCc)DCAFT}Solventl DCDCDCDCDCDCDCAFTOcdcl3w jDCAECjDCjDCAECjDCAECAFT}Sweep Width (Hz)o `<EC` EC`EC`<EC` EC` EC`<ECAFT14992.51{ -ECEEC9EC-ECEEC-ECEECAFT}Temperature (grad C)m gDECgJECgGECgDECgJECgJECgDECAFTe20.0000CuC4(DuC4(DCCC04(DuCDuCDC4(DC0DuC EuC ECDC0 EuC,EuC,EC EC0,EuCQEuCQEC,EC0CC4(DC4(DCCC04(DCtDCtDC4(DC0tDCDCDCtDC0DC,EC,ECDC0,ECQECQEC,ECM$?1~C~mD!$?2j:CcD!$?3nCYC诜D!%?13`CܓD!%?14CyD!%?15CLD!%? 16 DuD!%?17DuDD!%?18'#DD!%?19V2DPDyD!%?20gD?D!%?21LDxD!%?22DڑD!%?23ĆCD!%?24 DVD!%?25wDsD!%?26hDownD!%?27,DMZzD!?ud?eV??e?;3e????q?&? .1?O_;3? )H? E)$? ? ?  E)? ~RE)? UE)?Fe,B??V8?^Fe?MFe? 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