Bufadienolides. 13. Conversion of 3β-hydroxy-17-oxoandrost-5-ene to 3β-acetoxy-5β,14α-bufa-20,22-dienolide

George Pettit, Jerry R. Dias

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

A synthetic method was developed for converting the readily available dehydroepiandosterone (1a) to 3β-acetoxy-5β,14α-bufa-20,22-dienolide (11). Important steps in the transformation included condensation of ketone 1b with diethyl cyanomethylphosphonate to afford olefin 2. Selective reduction of olefin 2 provided formate 4 which was successively oxidized (5) and reduced to ketone 6b. Application of the Henbest reagent (trimethyl phosphite-chloroiridic acid) to reduction of ketone 6b provided a convenient pathway to 3β alcohol 7b. The remaining steps to bufadienolide 11 proceeded via intermediates 8, 9, and 10.

Original languageEnglish (US)
Pages (from-to)3207-3211
Number of pages5
JournalJournal of Organic Chemistry
Volume36
Issue number21
StatePublished - 1971

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Bufanolides
Ketones
trimethyl phosphite
formic acid
Alkenes
Condensation
Alcohols
Acids

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Bufadienolides. 13. Conversion of 3β-hydroxy-17-oxoandrost-5-ene to 3β-acetoxy-5β,14α-bufa-20,22-dienolide. / Pettit, George; Dias, Jerry R.

In: Journal of Organic Chemistry, Vol. 36, No. 21, 1971, p. 3207-3211.

Research output: Contribution to journalArticle

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