4,4-Dimethyl-A-homoandrostane epoxides

Abstract

Epimeric 3-hydroxy derivatives II and III were prepared on reduction of ketone I and then submitted to epoxidation. It was found that the 5(0)n participation of the 3α-oxygenated substituent leads to the formation of 3α, 5α-transannular epoxide IX both if the 5β,6β-epoxide VIII was opened with alkalies, or when the 5,6-double bond of the hydroxy derivative III was epoxidized, 3α,5α-Transannular epoxide XI was prepared as a substance with potential antiandrogenic activity.