Bufadienolides. 5. Synthesis of Cardenolides

George Pettit, Cherry L. Herald, John P. Yardley

Research output: Contribution to journalArticle

30 Scopus citations

Abstract

Boron trifluoride catalyzed lead tetraacetate oxidation of 30-acetoxy-2O-oxo-oa-pregnane and of pregnenolone acetate was employed to obtain the corresponding 21-acetoxy derivatives. Reaction of 3β,21-diacetoxy-20-oxo-5a-pregnane (1) with the anion prepared from diethyl cyanomethylphosphonate and subsequent treatment with hydrochloric acid afforded the corresponding nitrile (2) and derived imino lactone hydrochloride (3a). Acid hydrolysis of the imino lactone gave 3β-acetoxy-5<x-cardenolide (4b). Analogous transformation of ketone 6 provided 3β-acetoxy-A6-cardenolide (10b). The two-step reaction sequence from readily available a-hydroxy ketones provides a potentially useful route to imino lactones and butenolides.

Original languageEnglish (US)
Pages (from-to)1389-1392
Number of pages4
JournalJournal of Organic Chemistry
Volume35
Issue number5
DOIs
StatePublished - May 1 1970

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ASJC Scopus subject areas

  • Organic Chemistry

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