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 (alpha, alpha') and unsymmetrical structures (alpha,beta'), 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 5alpha- and 5beta-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.
Templeton
J F
JF
Faculty of Pharmacy, University of Manitoba, Winnipeg, Manitoba, Canada. templeto@ms.umanitoba
Majgier-Baranowska
H
H
Marat
K
K
D000735:Androstenedione / Q000031:analogs & derivatives* / Q000737:chemistry; D019281:Dimerization; D009682:Magnetic Resonance Spectroscopy; D008670:Metals / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013256:Steroids / Q000737:chemistry*
D008670:Metals; D013256:Steroids; C407746:methyl androst-4-ene-3,17-dion-19-oate; D000735:Androstenedione