Collect. Czech. Chem. Commun. 1998, 63, 1528-1542

Long-Range Effect of 17-Substituents in 3-Oxo Steroids on 4,5-Double Bond Hydrogenation

Romana Šídová, Karel Stránský, Alexander Kasal, Barbora Slavíková and Ladislav Kohout

Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic


The long-range effect of substituents in the 17-position on the hydrogenation of double bond of the steroidal ∆4-3-ketones in acetic acid on a platinum catalyst is described in a series of testosterone (1) and epitestosterone (5) esters with carboxylic acids of varying alkyl chain length. The ratio 5α- to 5β-products is affected by the nature of substituents in the position 17.

Keywords: Steroids; Long-range effect; 5α/5β Ratio; Hydrogenation; Circular dichroism; Gas chromatography.