Collect. Czech. Chem. Commun. 1996, 61, 1386-1395

trans-Hydrindanes by Reduction: Synthesis of Dihydro-B-nortestosterone

Alexander Kasala, Hana Chodounskáa and Wojciech J. Szczepekb

a Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic,166 10 Prague 6, Czech Republic
b Pharmaceutical Research Institute, Rydygiera 8, 01-793 Warsaw, Poland


Reduction with diimide was employed in the synthesis of potential antiandrogens - 17β-hydroxy-B-nor-5α-androstan-3-one (26) and its 17α-methyl derivative (25). Other methods of reduction (hydroboration, catalytic hydrogenation) were less effective.

Keywords: Diimide reduction; Stereochemistry; Catalytic hydrogenation.