Bufadienoiides. 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 journalArticlepeer-review

19 Scopus citations

Abstract

A synthetic method was developed for converting the readily available dehydroepiandosterone (la) to 3β-acetoxy-5β,14α-bufa-20,22-dienolide (11). Important steps in the transformation included condensation of ketone lb 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
DOIs
StatePublished - Oct 1 1971

ASJC Scopus subject areas

  • Organic Chemistry

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