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

George Pettit, D. S. Alkalay, P. Hofer, P. A. Whitehouse

Research output: Contribution to journalArticle

1 Citation (Scopus)

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
StatePublished - 1964
Externally publishedYes

Fingerprint

Biological Products
Cholanes
Steroids
Lanosterol
Pregnanes
Oxidation
Ketones
Degradation
androstane
chromium trioxide
20-oxo-pregnane

ASJC Scopus subject areas

  • Drug Discovery
  • Organic Chemistry
  • Biochemistry

Cite this

Pettit, G., Alkalay, D. S., Hofer, P., & Whitehouse, P. A. (1964). Steroids and related natural products-XXII. Oxidation of 3β-acetoxy-5α-lanostane. Tetrahedron, 20(7), 1755-1762.

Steroids and related natural products-XXII. Oxidation of 3β-acetoxy-5α-lanostane. / Pettit, George; Alkalay, D. S.; Hofer, P.; Whitehouse, P. A.

In: Tetrahedron, Vol. 20, No. 7, 1964, p. 1755-1762.

Research output: Contribution to journalArticle

Pettit, G, Alkalay, DS, Hofer, P & Whitehouse, PA 1964, 'Steroids and related natural products-XXII. Oxidation of 3β-acetoxy-5α-lanostane', Tetrahedron, vol. 20, no. 7, pp. 1755-1762.
Pettit, George ; Alkalay, D. S. ; Hofer, P. ; Whitehouse, P. A. / Steroids and related natural products-XXII. Oxidation of 3β-acetoxy-5α-lanostane. In: Tetrahedron. 1964 ; Vol. 20, No. 7. pp. 1755-1762.
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