title: Synthesis of 7β-hydroxy-epiandrosterone.
abstract: 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.
authors: Laboratoire de Transformations Chimiques et Pharmaceutiques, UMR7084, Conservatoire National des Arts et Métiers, 2 rue Conté, 75003 Paris, France.
authors: Christophe
authors: C
authors: Ricco
authors: Gilbert
authors: G
authors: Revial
authors: Clotilde
authors: C
authors: Ferroud
authors: Olivier
authors: O
authors: Hennebert
authors: Robert
authors: R
authors: Morfin
mesh_terms: D000738:Androsterone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: C531236:7-hydroxyandrosterone; D000738:Androsterone