Steroids p. 141 - 144 (1993)
Update date:2022-08-29
Topics:
Davioud
Schambel
Viger
Marquet
We describe the synthesis of 13β- and 13α-H-18-nor-androst-4-ene-3,17- dione (1a and 1b) from 18-hydroxyprogesterone (18 → 20) hemiketal, via the 18-acetoxy-17β-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.
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(1988)
