Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Steroid Series. VII. Synthesis of 6-Methyl-B-norsteroids.
Rinji Takasaki
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JOURNAL FREE ACCESS

1962 Volume 10 Issue 6 Pages 439-445

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Abstract

3β, 5-Dihydroxy-6β-formyl-B-nor-5β-steroids (IIIa, b, c) of cholestane, pregnane, and androstane series were converted into the corresponding 3β, 5-dihydroxy-6β-methyl-B-nor-5β-steroids (VIa, d, e) by reduction of (III) with sodium borohydride, followed by tosylation of 6-hydroxymethyl group and subsequent treatment with lithium aluminium hydride. The compounds (VI) were oxidized to 3-oxo-5-hydroxy-6β-methyl-B-nor-5β-steroid derivatives (VIIa, b, f) which were then dehydrated to 6ξ-methyl-B-norcholest-4-en-3-one (VIIIa), 6ξ-methyl-B-norpregn-4-ene-3, 20-dione (VIIIb), and 6ξ-methyl-B-norandrost-4-ene-3, 17-dione (VIIIf).

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© The Pharmaceutical Society of Japan
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