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Chemical syntheses of 5α-cholesta-6,8(14)-dien-3β-ol-15-one and related 15-oxygenated sterols

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

Publisher
Elsevier Science
Year
1979
Tongue
English
Weight
785 KB
Volume
25
Category
Article
ISSN
0009-3084

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✦ Synopsis

Hydroboration of 5a-cholesta-8,14-dien-3fl-ol ( ) gav e 5a-cholest-8-en-3CLl5a-diol (IV) in 89% yield. 5a-Cholest-7-en-3/3,15a-diol (V) was prepared in 91% yield by hydroboration of 5ct-cholesta-7,14-dien-3/3-ol (H). Hydroboration of 27:63 mixture of I and H gave IV and V in 18% and 70% yields, respectively. 5a-Cholest-8-en-15a-ol-3-one and 5a-cholest-7-en-15ct-ol-3one were prepared in high yields from IV and V, respectively, by either selective oxidation with silver carbonate-celite or by enzymatic oxidation using cholesterol oxidase. 7a,Sa-Epoxy-Sc~cholestan-3/3,15a-diol (VIII) was prepared in 93% yield by treatment of V with m-chloroperbenzoic acid. 5t~-Cholest-8( )-en-7a-ol-3,15-dione (IX) was prepared in 56% yield by oxida tion of VIII with pyridinium chlorochromate followed by treatment of the crude product with acid. Compound IX was also obtained in 72% yield by selective chemical oxidation of 5ct-cholest-8( )-en-3/3,7a,15ot-triol. 5a-Cholesta~6,8( )-dien-3,15-dione (X) was prepared in 89% yield by treatment of IX with p-toluenesulfonic acid under controlled conditions. Reduction of X with lithium tri-tert-butoxyaluminum hydride under controlled conditions gave 5a-cholesta-6,8(14)-dien-3/3-ol-15-one in 84% yield.

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