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An improved synthesis of 18-norandrost-4-ene-3,17-dione
E Davioud1, P Schambel, A Viger
1Laboratoire de Chimie Organique Biologique, URA CNRS 493, Université Pierre et Marie Curie, Paris, France.
Steroids
|March 1, 1993
Abstract:
We describe the synthesis of 13 beta- and 13 alpha-H-18-nor-androst-4-ene-3,17-dione (1a and 1b) from 18-hydroxyprogesterone (18-->20) hemiketal, via the 18-acetoxy-17 beta-hydroxyandrost-4-en-3-one formed by a modified Baeyer-Villiger reaction. Saponification of 18-acetoxyandrost-4-ene-3,17-dione with sonication, then retroaldolization in the presence of a formaldehyde trap, methone, afforded the mixture of 1a and 1b with 80% yield in a "one-pot" procedure and at room temperature. This yield was greatly improved, compared with the already published procedure.