Hydrogenation of a Tetrasubstituted Double Bond: Synthesis of 5-Methyl-19-nor-5β-pregnanes

Abstract

Reduction of C=C and/or C=O bonds in 5-methyl-19-nor-5β-pregn-9-ene-3,20-dione (1) leads to saturated and unsaturated ketones and hydroxy ketones. The C=C reduction affords mainly 9β,10β and 9α,10β dihydro products. Reaction conditions of partial esterification, hydrolysis and oxidation were elaborated. Several analogues were prepared for the testing of gestagenic and neurosteroidal activities.