Steroids and Related Natural Products. 69. Synthesis of 20(22)-Dihydro-23-deoxodigitoxigenin

F. Warren Villaescusa, George Pettit

Research output: Contribution to journalArticle

8 Scopus citations

Abstract

A synthetic route from digitoxigenin to 20(22)-Vdihydro-23-deoxodigitoxigenin (10a) has been developed. Digi-toxigenin was acetylated, dehydrated, and selectively hydrogenated to give 3β-acetoxy-5β;20-card-14-enolide (4). Reduction with lithium aluminum hydride gave diol 5 which was cyclized to yield 3β-hydroxy-23-deoxo-5β,20-card-14-enolide (6). Introduction of the 14β-hydroxyl (10a) group was achieved by successive formation of the 14β-hydroxy-15α-bromo (7) and β-epoxide (8) derivatives followed by a reduction step.

Original languageEnglish (US)
Pages (from-to)569-572
Number of pages4
JournalJournal of Organic Chemistry
Volume37
Issue number4
DOIs
StatePublished - Feb 1 1972

ASJC Scopus subject areas

  • Organic Chemistry

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