Reaction of the steroidal sapogenin spiroketal system with ethanedithiol

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

Research output: Contribution to journalArticle

30 Citations (Scopus)

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
StatePublished - 1959
Externally publishedYes

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Sapogenins
Desulfurization
boron trifluoride etherate
1,2-ethanedithiol
spiroketal

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Reaction of the steroidal sapogenin spiroketal system with ethanedithiol. / Djerassi, Carl; Halpern, O.; Pettit, George; Thomas, G. H.

In: Journal of Organic Chemistry, Vol. 24, No. 1, 1959, p. 1-6.

Research output: Contribution to journalArticle

Djerassi, Carl ; Halpern, O. ; Pettit, George ; Thomas, G. H. / Reaction of the steroidal sapogenin spiroketal system with ethanedithiol. In: Journal of Organic Chemistry. 1959 ; Vol. 24, No. 1. pp. 1-6.
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