Steroids and related natural products-XXII. Oxidation of 3β-acetoxy-5α-lanostane

G. R. Pettit, D. S. Alkalay, P. Hofer, P. A. Whitehouse

Research output: Contribution to journalArticle

1 Scopus citations

Abstract

Chromium trioxide oxidation of 3β-acetoxy-5α-lanostane (IVa) has been evaluated as a route to 3β-acetoxy-20-oxo-4,4,14α-trimethyl-5α-pregnane (VI) and 3β-acetoxy-17-oxo-4,4,14-α-trimethyl-5α-androstane (VIIa). One of the principal oxidation products was 3β-acetoxy-25-oxo-5α-27-norlanostane (V). Transformation of 25-ketone V to 3β,24-dihydroxy-4,4,14α-trimethyl-5α-cholane (VIIIa) confirmed the structural assignment. Although small amounts of 20-oxo-pregnane VI and 17-oxo-androstane VIIa were detected among the oxidation products, stepwise degradation of lanosterol was considered a more satisfactory route to these substances.

Original languageEnglish (US)
Pages (from-to)1755-1762
Number of pages8
JournalTetrahedron
Volume20
Issue number7
DOIs
StatePublished - 1964
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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