Reaction of the Steroidal Sapogenin Spiroketal System with Ethanedithiol1

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

doi:10.1021/jo01083a001

Reaction of the Steroidal Sapogenin Spiroketal System with Ethanedithiol¹

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

Research output: Contribution to journal › Article › peer-review

32 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 language	English (US)
Pages (from-to)	1-6
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	24
Issue number	1
DOIs	https://doi.org/10.1021/jo01083a001
State	Published - Jan 1 1959
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo01083a001

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title = "Reaction of the Steroidal Sapogenin Spiroketal System with Ethanedithiol1",

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.",

author = "Carl Djerassi and O. Halpern and Pettit, {George R.} and Thomas, {G. H.}",

year = "1959",

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AU - Djerassi, Carl

AU - Halpern, O.

AU - Pettit, George R.

AU - Thomas, G. H.

PY - 1959/1/1

Y1 - 1959/1/1

N2 - 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.

AB - 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.

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Reaction of the Steroidal Sapogenin Spiroketal System with Ethanedithiol¹

Abstract

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