Collect. Czech. Chem. Commun. 1991, 56, 1070-1086

A-homo-B,19-dinorandrostanes from 6β-methanesulfonyloxy-5-methyl-19-nor-5β-androst-9-ene derivatives

Alexander Kasala, Jaroslav Podlahab and Jaroslav Zajíčeka

a Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6
b Department of Organic Chemistry, Charles University, 128 40 Prague 2


6β-Methanesulfonyloxy derivatives of 5-methyl-19-nor-5β-androst-9-enes with different oxygen functionalities in positions 3β and 17 ( compounds IX and XVII) were converted to 4a-methyleno-A-homo-B,19-dinor-5β-androst-9-ene derivatives (compounds X, XX and XXI) which were hydrogenated to give derivatives of 4aα-methyl-A-homo-5,19-dinor-5β,10α-androstane (XXII, XXIII) and 4aα-methyl-A-homo-B,19-dinor-5α,9β-androstane (XXIV, XXV). The structure of the latter compounds has been confirmed by X-ray diffraction of diketone XXVII which has been shown, in accordance with calculations by the MM2 method, to exist in a boat conformation of the ring C. The 17β-hydroxy-3-ketone XXX exhibits in vivo antiandrogenic activity.