Abstract
The mixture of enol acetates (II and III) of 16-acetyl-estrone-3-methyl ether underwent hydrogenolysis under high pressure (100kg/cm2) of hydrogen in the presence of Raney Ni to form the 16β-ethyl-17β-ol compound (X) in high yield. The mechanism of hydrogenolysis was discussed. This facile and stereoselective introduction of 16β-ethyl and 17β-hydroxy groups was applied to the synthesis of 16β-ethyl-19-nortestosterone (TSAA-291, XIX), which shows strong antiandrogenic activity.
