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Sterol synthesis. A novel reductive rearrangement of an α,β-unsaturated steroidal epoxide; a new chemical synthesis of 5α-cholest-8(14)-en-3β,15α-diol

✍ Scribed by Edward J. Parish; George J. Schroepfer Jr.

Publisher
Elsevier Science
Year
1977
Tongue
English
Weight
451 KB
Volume
18
Category
Article
ISSN
0009-3084

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✦ Synopsis

Reduction of 3t3-benzoyloxy-14a,15c~-epoxy-5c~-cholest-7-ene with either lithium triethylborohydride or lithium aluminum hydride (4 molar excess) gave 5c~-cholest-8( 14)-en-3~,15a-diol in high yield. Reduction of the epoxy ester with lithium triethylborodeuteride or lithium aluminum deuteride (4 molar excess) gave [7c~-2H]-5a-cholest-8( 14)-en-3/3,15c~-diol. Reduction of 3/3-benzoyloxy-14c~,15a-epoxy-5a-cholest-7-ene with a large excess (24 molar excess) of lithium aluminum hydride gave, in addition to the expected 5a-cholest-8( 14)-en-3/3,15a-diol, a significant yield (33%) of 5c~-cholest-8( 14)-en-3fl-ol. Reduction of the epoxy ester with a large excess (24 molar excess) of lithium aluminum deuteride gave [7c~-2H]-5a-cholest-8( 14)-en-3#,15a-diol and 5c~-cholest-8( 14)-en-3#-ol which contained two atoms of stably bound deuterium.

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