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Concerning the chemical synthesis of 3β-hydroxy-5α-cholest-8(14)-en-15-one, a novel regulator of cholesterol metabolism

✍ Scribed by William K. Wilson; Ker-Shi Wang; Alemka Kisic; George J. Schroepfer Jr.

Publisher
Elsevier Science
Year
1988
Tongue
English
Weight
866 KB
Volume
48
Category
Article
ISSN
0009-3084

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✦ Synopsis

A four-step synthesis of 3 beta-hydroxy-5 alpha-cholest-8(14)-en-15-one (I) from 7-dehydrocholesterol is described. This synthesis, which is efficient and suitable for kilogram scale work, was carried out in a 33% overall average yield (39% overall best yield). A major byproduct of the hydrolysis of 3 beta-benzoyloxy-14 alpha,15 alpha-epoxy-5 alpha-cholest-7-ene to I was found to be the ring C aromatic sterol 12-methyl-18-nor-5 alpha-cholesta-8,11,13-trien-3 beta-ol. Several other intermediates and byproducts of these reactions were also identified. All new sterols were characterized by 1H- and 13C-NMR.

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