Abstract
Reduction of 3β-benzoyloxy-14α,15α-epoxy-5α-cholest-7-ene with either lithium triethylborohydride or lithium aluminum hydride (4 molar excess) gave 5α-cholest-8(14)-en-3β,15α-diol in high yield. Reduction of the epoxy ester with lithium triethylborodeuteride or lithium aluminum deuteride (4 molar excess) gave [7 α- 2H]-5α-cholest-8(14)-en-3β,15α-diol. Reduction of 3β-benzoyloxy-14α,15α-epoxy-5α-cholest-7-ene with a large excess (24 molar excess) of lithium aluminum hydride gave, in addition to the expected 5α-cholest-8(14)-en-3β,15α-diol, a significant yield (33%) of 5α-cholest-8(14)-en-3β-ol. Reduction of the epoxy ester with a large excess (24 molar excess) of lithium aluminum deuteride gave [7 α- 2H]-5α-cholest-8(14)-en-3β,15α-diol and 5α-cholest-8(14)-en-3β-ol which contained two atoms of stably bound deuterium.
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