Collect. Czech. Chem. Commun. 1983, 48, 2040-2050

Preparation and pharmacological properties of 4,5-secopregnane-3,20-dione and its derivatives

Alexander Kasala, Luboš Stárkab, Richard Hamplb and Ladislav Kohouta

a Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6
b Endocrinological Research Institute, 116 94 Prague 1


20β-Benzoyloxy-4-pregnen-3-one was oxidized to seco acid VI which was deoxygenated in the position 5 and converted to methyl ketone XI. This substance was oxidized directly to 4,5-secodihydroprogesterone and also converted to 17α-acetoxy derivative XXI via the corresponding monoketal XV. Compounds XIV and XXI do not display a gestagenic activity or an antiandrogenic activity either.