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Inhibitors of sterol synthesis. Synthesis of [2,4-3H]5α-cholest-8(14)-ene-3β,7α,15α-triol and [2,4-3H]5α-cholest-8(14)-en-38-ol-15-one

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

Publisher
John Wiley and Sons
Year
1981
Tongue
French
Weight
301 KB
Volume
18
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

Oxidation of 5α‐cholest‐8(14)‐ene‐3β,7α,15α‐triol with silver carbonate‐celite gave 5α‐cholest‐8(14)‐ene‐7α,15α‐diol‐3‐one in 88% yield. Treatment of the latter compound with tritiated water under basic conditions gave a labeled product which was reduced with lithium tri‐tert‐butoxyaluminum hydride in tetrahydrofuran to give [2,4–H]5α‐cholest‐8(14)‐ene‐3β,7α,15α‐triol which was obtained in high purity after medium pressure liquid chromatography in the form of its triacetate derivative. Treatment of the labeled triol with concentrated hydrochloric acid in 95% ethanol gave the desired [2,4‐^3^H]5α‐cholest‐8(14)‐en‐3β‐ol‐15‐one.

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