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Synthesis of the C-10 epimeric alcohols 46a and 46b. a, 1: LiAlH4, THF, 0°C; 2: NaH, p-methoxybenzyl chloride, DMF, RT; 3: OsO4 cat., NMO, acetone, H2O, RT; 4: NaIO4, RT, 74% over four steps. b, AllylMgBr, dimethoxyethane, -78°C, 99%, d.r. = 8:1. c, MOMCl, N,N-diisopropylethylamine, DMAP cat., CH2Cl2, RT, 88%. d, 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone, aqueous pH 7 phosphate buffer, CH2Cl2, RT, 93%.
