1alpha,2alpha-Epoxy-25-hydroxycholesta-4,6-dien-3-one → 1alpha,25-Dihydroxycholesta-4,6-dien-3-one

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Reaction Steps

The epoxide from (b) was treated with zinc dust and acetic acid as described in Example 2 (a) to yield 1α,25-dihydroxycholesta-4,6-dien-3-one, which was then converted to the trimethylsilyl ether and reduced with lithium/liquid ammonia as described in Example 2 (b). The title compound obtained in this way, (m.p. 171-173 solidifies and remelts at 178°-179°; [α]D -35° in CHCl2) exhibited n.m.r. peaks at δ0.68, 1.02 (methyl groups), δ1.18 (gem-dimethyl groups), δ3.83 (1 proton, narrow signal, 1β-H), δ3.6-4.3 (1 proton, broad signal, 3α-H) and δ5.57 (1-proton, multiplet, 6-H). The 3-monobenzoate thereof melts at 212°-216°; [α]D -20° in CHCl3).

Provenance & Evidence