Synthesis of 7β-hydroxy-epiandrosterone.
The synthesis of 7β-hydroxy-epiandrosterone (6) possessing strong anti-inflammatory properties was achieved starting from 3β-acetoxy-17,17-(ethylenedioxy)-5-androsten (1). This approach involved as a main step an allylic oxidation of the C-7 followed by two reduction reactions of the double bond and of the carbonyl group. This stereoselective synthesis in 5 steps gave 7β-hydroxy-epiandrosterone in 63% overall yield.
Ricco
Christophe
C
Laboratoire de Transformations Chimiques et Pharmaceutiques, UMR7084, Conservatoire National des Arts et Métiers, 2 rue Conté, 75003 Paris, France.
Revial
Gilbert
G
Ferroud
Clotilde
C
Hennebert
Olivier
O
Morfin
Robert
R
D000738:Androsterone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
C531236:7-hydroxyandrosterone; D000738:Androsterone