Trans hydrindanes by dimide reduction: Synthesis of dihydro-B-nortestosterone and its 17α-methyl derivative

Article abstract of DOI:10.1016/0040-4039(96)01328-7

Reductive hydroboration of Δ⁵-B-norsteroids (e.g., 1) affords 5α-dihydro products (e.g., 3) in a low yield. Better yields, were obtained by reduction with diimide. The method was employed in the synthesis of potential antiandrogens - 17β-hydroxy-B-nor-5α-androstan-3-one (8) and its 17α-methyl derivative (9).