An Unusual Backbone Rearrangement. The Formation of 5α,17α-cholest-14-en-3β-ol Acetate from 5α-Cholest-8(14)-en-3β-ol Acetate

Eliahu Caspi; William L. Duax; Jane F. Griffin; Jacques P. Moreau; Thomas A. Wittstruck

doi:10.1021/jo00901a034

An Unusual Backbone Rearrangement. The Formation of 5α,17α-cholest-14-en-3β-ol Acetate from 5α-Cholest-8(14)-en-3β-ol Acetate

Eliahu Caspi
, William L. Duax
, Jane F. Griffin
, Jacques P. Moreau
, Thomas A. Wittstruck

Department of Structural Biology

University of Massachusetts Medical School
Hauptman-Woodward Medical Research Institute, Inc.

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

23 Scopus citations

Abstract

The acid-catalyzed isomerization of 5α-cholest-8(14)-en-3β-ol acetate (and 3β-benzoate) at -78° results in 5α,17α-cholest-14-en-3β-ol acetate (or 3β-benzoate); hydrogenation (¹H₂,²H₂) gave a product which on the basis of ¹³C NMR was tentatively assigned as 5α,14β,17α-cholestan-3β-ol.

Original language	English
Pages (from-to)	2005-2006
Number of pages	2
Journal	Journal of Organic Chemistry
Volume	40
Issue number	13
DOIs	https://doi.org/10.1021/jo00901a034
State	Published - Jun 1 1975

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@article{039928ac3e194949acdd277cfdbf17e5,

title = "An Unusual Backbone Rearrangement. The Formation of 5α,17α-cholest-14-en-3β-ol Acetate from 5α-Cholest-8(14)-en-3β-ol Acetate",

abstract = "The acid-catalyzed isomerization of 5α-cholest-8(14)-en-3β-ol acetate (and 3β-benzoate) at -78° results in 5α,17α-cholest-14-en-3β-ol acetate (or 3β-benzoate); hydrogenation (1H2,2H2) gave a product which on the basis of 13C NMR was tentatively assigned as 5α,14β,17α-cholestan-3β-ol.",

author = "Eliahu Caspi and Duax, \{William L.\} and Griffin, \{Jane F.\} and Moreau, \{Jacques P.\} and Wittstruck, \{Thomas A.\}",

year = "1975",

month = jun,

day = "1",

doi = "10.1021/jo00901a034",

language = "English",

volume = "40",

pages = "2005--2006",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "13",

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T1 - An Unusual Backbone Rearrangement. The Formation of 5α,17α-cholest-14-en-3β-ol Acetate from 5α-Cholest-8(14)-en-3β-ol Acetate

AU - Caspi, Eliahu

AU - Duax, William L.

AU - Griffin, Jane F.

AU - Moreau, Jacques P.

AU - Wittstruck, Thomas A.

PY - 1975/6/1

Y1 - 1975/6/1

N2 - The acid-catalyzed isomerization of 5α-cholest-8(14)-en-3β-ol acetate (and 3β-benzoate) at -78° results in 5α,17α-cholest-14-en-3β-ol acetate (or 3β-benzoate); hydrogenation (1H2,2H2) gave a product which on the basis of 13C NMR was tentatively assigned as 5α,14β,17α-cholestan-3β-ol.

AB - The acid-catalyzed isomerization of 5α-cholest-8(14)-en-3β-ol acetate (and 3β-benzoate) at -78° results in 5α,17α-cholest-14-en-3β-ol acetate (or 3β-benzoate); hydrogenation (1H2,2H2) gave a product which on the basis of 13C NMR was tentatively assigned as 5α,14β,17α-cholestan-3β-ol.

UR - https://www.scopus.com/pages/publications/0016862989

U2 - 10.1021/jo00901a034

DO - 10.1021/jo00901a034

M3 - Letter

C2 - 1133610

AN - SCOPUS:0016862989

SN - 0022-3263

VL - 40

SP - 2005

EP - 2006

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 13

ER -

An Unusual Backbone Rearrangement. The Formation of 5α,17α-cholest-14-en-3β-ol Acetate from 5α-Cholest-8(14)-en-3β-ol Acetate

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