Studies of the synthesis of 5-hydroxy 6-keto steroids and related 6-keto steroids

Syntheses of 5-hydroxy-5α- and 5β-cholestan-6-one (11 and 13 ) and their 3β-acetoxy ( 10 and 21 ) and 3β-benzyloxy derivatives ( 12 and 19 ) are described, as are syntheses of the 7α-deutero derivatives of 10 and 21 . Related investigations of the syntheses of the 5-methoxy and 5-methyl analogues of...

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Bibliographic Details
Published in:Canadian journal of chemistry 1987-09, Vol.65 (9), p.2203-2216
Main Authors: Yates, Peter, Stiver, Shirley
Format: Article
Language:English
Subjects:
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
Steroids
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Summary:Syntheses of 5-hydroxy-5α- and 5β-cholestan-6-one (11 and 13 ) and their 3β-acetoxy ( 10 and 21 ) and 3β-benzyloxy derivatives ( 12 and 19 ) are described, as are syntheses of the 7α-deutero derivatives of 10 and 21 . Related investigations of the syntheses of the 5-methoxy and 5-methyl analogues of these compounds are also discussed. Treatment of 12 with potassium tert-butoxide has been shown to give 5-hydroxy-5β-cholest-3-en-6-one ( 14 ) and its Δ 2 isomer 15 . Reaction of 6-nitrocholesteryl acetate ( 50 ) with lithium dimethylcuprate gives 3α,5-cyclo-5α-cholestan-6-one (E)-oxime ( 51 ) as the major product.
ISSN:0008-4042
1480-3291
DOI:10.1139/v87-369