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Sterol biosynthesis: Establishment of the structure of 3β-p-bromobenzoyloxy-5α-cholest-8(14)-en-15β-ol

✍ Scribed by George N. Phillips Jr.; Florante A. Quiocho; Ronald L. Sass; Peter Werness; Herschell Emery; Furn F. Knapp Jr.; G.J. Schroepfer Jr.


Publisher
Elsevier Science
Year
1976
Tongue
English
Weight
593 KB
Volume
5
Category
Article
ISSN
0045-2068

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The chemical synthesis of 3beta-bromobenzoyloxy-14alpha, 15alpha-epoxy-5alpha-cholest-7-ene is described. Single crystal structral analysis was employed to unambiguously determine the location and absolute configuration of the epoxide moiety in the 3beta-p-bromobenzoyloxy-14alpha, 15alpha-epoxy-5alp

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## 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__‐butoxy

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The X-ray crystal structure of 3~-benzoyloxy-6a-chloro-5a-cholest-7-ene (IV) was determined by the heavy atom method and ref'med to R ---0.063 (space group P2s, a --11.364, b = 11.089, c --12.232,/~ = 99.43 °, Z ---2). IV was previously shown to be an important intermediate in the acid-catalyzed iso

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