Synthesis of some 1,2-unsaturated analogues of androgens with the cyclopropane ring in 4,5-position

Abstract

1,2-Unsaturated analogues of testosterone XI and XVII carrying the cyclopropane ring in position 4,5 were prepared from the corresponding 3-oxo derivatives VIII and XIV viathe enol acetates IX and XV and the bromo ketones X and XVI followed by dehydrohalogenation with sym-collidine. Analogues of androstenedione XXI and testosterone XIX with the epoxide ring in 2β,19-position were prepared from the bromo ketone XVI with potassium methoxide.