H. Chodounska et al., ON STEROIDS .372. SYNTHESIS OF SOME EPITESTOSTERONE ANALOGS, Collection of Czechoslovak Chemical Communications, 59(2), 1994, pp. 435-443
11beta-Hydroxyandrost-4-ene-3,17-dione (III) was converted into a pote
ntial metabolite of epitestosterone - 11beta, 17alpha-dihydroxyandrost
-4-en-3-one (II) in 5 steps, including the inversion of configuration
of a 17beta-hydroxy group. This inversion was not feasible in the prep
aration of the analogues X, XIV, XX, and XXII, where the 17alpha-hydro
xy group was introduced first and only then was the rest of the molecu
le modified.