Conversion of carbonyl steroid derivatives to 1,1-dibromoalkenes by the catalytic olefination reaction and synthesis of functionally substituted steroids on their basis

Abstract

Catalytic olefination of carbonyl steroid derivatives were used to obtain the corresponding 1,1-dibromoalkenes. For this, N-unsubstituted steroid hydrazones were involved into the reaction with tetrabromomethane in the presence of copper(i) chloride. The dibromides can be used for the synthesis of various functionalized steroids by conversion of a dibromomethylidene fragment to the carboxy, amide, and phosphonate groups.