Reaction of the Steroidal Sapogenin Spiroketal System with Ethanedithiol1

Carl Djerassi, O. Halpern, George R. Pettit, G. H. Thomas

Research output: Contribution to journalArticle

30 Scopus citations

Abstract

Ethanedithiol in the presence of boron trifluoride etherate reacts with the spiroketal system of steroidal sapogenins to form the corresponding furostane 26-ethylenethioketal. Desulfurization leads to the furostane which in the 5α series was transformed into cholestan-16β-ol. Structural formulas are proposed to explain these reactions.

Original languageEnglish (US)
Pages (from-to)1-6
Number of pages6
JournalJournal of Organic Chemistry
Volume24
Issue number1
DOIs
StatePublished - Jan 1 1959
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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