- An improved synthesis of 18-norandrost-4-ene-3,17-dione
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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.
- Davioud,Schambel,Viger,Marquet
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- SYNTHESIS OF 18-SUBSTITUTED ANDROST-4-EN-3-ONE DERIVATIVES AS POTENTIAL INHIBITORS OF ALDOSTERONE BIOSYNTHESIS
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Androst-4-en-3-one derivatives substituted at the 18-methyl group bearing a 17-keto or 17-spirolactone function have been synthesized and tested in vitro as inhibitors of aldosterone biosynthesis
- Viger, Antoinette,Coustal, Suzy,Schambel, Philippe,Marquet, Andree
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p. 7309 - 7322
(2007/10/02)
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