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The oxidative rearrangement of 5α-cholestan-3-one

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
20
Issue
3
Identifiers
DOI: 10.1016/s0040-4020(01)98633-8

Abstract

Abstract Treatment of 5α-cholestan-3-one (I) with hydrogen peroxide and selenic acid, followed by esterification, leads to 2α-carbomethoxy-A-nor-5α-cholestane (II) as the major product. Two other products also isolated are 3β-carbomethoxy-A-nor-5α-cholestane (IVa) and methyl 2,3-seco-5α-cholestane-2,3-dioate (Va). These facts are discussed in terms of a possible reaction mechanism.

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