Steroid dimer formation: metal reduction of Methyl Androst-4-ene-3,17-dion-19-oate

Two isomeric dimeric steroids, 3,3′-bis(methyl 3-hydroxyandrost-4-en-17-on-19-oate-3-yl), with symmetrical (α,α′) and unsymmetrical structures (α,β′), have been obtained by reduction of methyl androst-4-ene-3,17-dion-19-oate with zinc in aqueous acetic acid together with the major products, the isom...

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Bibliographic Details
Published in:Steroids 2000-04, Vol.65 (4), p.219-223
Main Authors: Templeton, John F, Majgier-Baranowska, Helena, Marat, Kirk
Format: Article
Language:English
Subjects:
Alicyclic compounds, terpenoids, prostaglandins, steroids
Androstenedione - analogs & derivatives
Androstenedione - chemistry
Bisteroid
Chemistry
Dimer
Dimerization
Exact sciences and technology
Magnetic Resonance Spectroscopy
Metals - chemistry
Molecular Structure
Organic chemistry
Oxidation-Reduction
Preparations and properties
Reduction
Steroids
Steroids - chemistry
Trimethylsilylation
Zinc
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Summary:Two isomeric dimeric steroids, 3,3′-bis(methyl 3-hydroxyandrost-4-en-17-on-19-oate-3-yl), with symmetrical (α,α′) and unsymmetrical structures (α,β′), have been obtained by reduction of methyl androst-4-ene-3,17-dion-19-oate with zinc in aqueous acetic acid together with the major products, the isomeric methyl 5α- and 5β-androst-3-en-17-on-19-oates. The structures of the dimers and unsaturated products are supported by spectroscopic methods. The symmetrical dimer was also obtained from treatment of the 4-en-3-on-19-oate ester with lithium in ammonia.
ISSN:0039-128X
1878-5867
DOI:10.1016/S0039-128X(99)00108-7