Collect. Czech. Chem. Commun. 1989, 54, 1318-1326

Antiandrogenic A-homo-B,19-dinor-analogues of androgens from 6β-chloro-5-methyl-19-nor-5β-androst-9-enes

Alexander Kasal

Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6


6β-Chloro derivatives of 5-methyl-19-nor-5β-androst-9-enes (Westphalen diol type) with oxygen functionalities in positions 3 and 17 were converted into diene VI by treatment with lithium aluminium hydride. The lipophilic product of hydrogenation of VI was shown to be 4aα-methyl-A-homo-B,19-dinor-5β,10α-androstane-3β,17β-diol (IX). Various paths leading to dihydrotestosteron analogues, e.g. selective acylation or oxidation of diol IX and partial hydrolysis of diacetate X, have been realized. 17β-Hydroxy-4aα-methyl-A-homo-B,19-dinor-5β,10α-androstan-3-one (XVI) has been found to exhibit antiandrogenic activity.