Collect. Czech. Chem. Commun. 1994, 59, 435-443

Synthesis of Some Epitestosterone Analogues

Hana Chodounská, Barbora Slavíková and Alexander Kasal

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


11β-Hydroxyandrost-4-ene-3,17-dione (III) was converted into a potential metabolite of epitestosterone - 11β,17α-dihydroxyandrost-4-en-3-one (II) in 5 steps, including the inversion of configuration of a 17β-hydroxy group. This inversion was not feasible in the preparation of the analogues X, XIV, XX, and XXII, where the 17α-hydroxy group was introduced first and only then was the rest of the molecule modified.