The chemistry of thujone. VIII. Thujone as a chiral synthon for the synthesis of optically active steroid analogues. The enol lactone route

Abstract

AbstractThe thujone‐derived enone 1 is converted via enol lactone intermediates 4 and 5 to the optically active steroidal analogue 13 and the corresponding 19‐norsteroid analogue 14. The structure of 13 was determined by X‐ray diffraction analysis. The acid‐catalyzed cyclopropane‐ring opening of 13 and ozonolysis of the resulting olefin provided the 16‐keto‐steroid analogue 18.