Collect. Czech. Chem. Commun. 1990, 55, 2510-2520

Epimeric 17-hydroxy derivatives of 14β-androst-5-en-3β-yl acetate

Ivan Černý, Vladimír Pouzar, Miloš Buděšínský, Pavel Drašar and Miroslav Havel

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


A new, six-step synthesis of 3β-hydroxy-14β-androst-5-en-17-one (IX) starting from 3β-hydroxyandrost-5-en-17-one has been elaborated. Reduction of acetate X with sodium borohydride afforded 17α-hydroxy-14β-androst-5-en-3β-yl acetate (XI). The corresponding 17β-derivative XIV was obtained by epimerization of 17α-O-tosyl derivative XIII with sodium nitrite in hexamethylphosphoramide. The 13C and 1H NMR spectra of 14β-androstane derivatives are discussed.