The Journal of Organic Chemistry

A novel synthesis of spironolactone. An application of the hydroformylation reaction

PGM Wuts, AR Ritter

Index: Wuts, Peter G. M.; Ritter, Allen R. Journal of Organic Chemistry, 1989 , vol. 54, # 21 p. 5180 - 5182

Full Text: HTML

Citation Number: 37

Abstract

Spironolactone (I), an aldosterone antagonist introduced in the late 1950s is a high-volume diuretic and belongs to a growing class of steroidal spirolactones.'Our interest in this class of lactones has lead us to develop a new approach to spironolactone from the readily available acetylene adduct 2. We thought that hydroformylation2 of ethisterone 2 would lead to the lactol3, which would give lactone 8 upon oxidation. Initial attempts at hydroformylating ...