Collect. Czech. Chem. Commun. 1993, 58, 2202-2210

Synthesis of 17α-Hydroxy Steroids: B-Norepitestosterone

Alexander Kasal

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


The key intermediate VI was prepared by two ways: by B ring contraction of an androst-5-ene-3β,17α-diol derivative I and by configurational inversion of the 17β-hydroxy group in a B-norandrost-5-ene-3β,17β-diol derivative XII. B-Norepitestosterone (IX) and its potentional metabolite X were then prepared by standard methodology. Both these compounds appear to be inhibitors of 5α-reductase.