[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:20][C@H:21]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[C:28]([O:34][CH2:35][CH2:36][CH2:37][O:38][CH3:39])[CH:27]=1)[CH:22]([CH3:24])[CH3:23])[C:10](=[O:19])[CH2:11][C@@H:12]([CH:16]([CH3:18])[CH3:17])[C:13](O)=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCC(C)[BH-](C(C)CC)C(C)CC.[K+]>O1CCCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]([C@@H:10]1[CH2:11][C@@H:12]([CH:16]([CH3:18])[CH3:17])[C:13](=[O:14])[O:19]1)[CH2:20][C@H:21]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[C:28]([O:34][CH2:35][CH2:36][CH2:37][O:38][CH3:39])[CH:27]=1)[CH:22]([CH3:24])[CH3:23])([CH3:4])([CH3:3])[CH3:2]A solution of 5.51 g of (2S,5S,7S)-5-tert-butoxycarbonylamino-2-isopropyl-7-[4-methoxy-3-(3-methoxypropoxy)-benzyl]-8-methyl-4-oxo-nonanoic acid in 25 mL of tetrahydrofuran is cooled to −30° C. and 10 mL of a 1.0 M solution of K-selectride in tetrahydrofuran is added dropwise within 30 minutes. The mixture is stirred for 2 hours at 30° C. and warmed to 0° C. and stirred for 16 hours. The reaction mixture is quenched with 50 mL of 1.0 M hydrochloric acid and extracted three times with 100 mL of dichloromethane. The organic layer is dried and the solvent is removed to give the title compound as a semi solid.
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