Synthesis of bridged steroids. II. Steroids having a bridged bicyclo[3.2.1]octane ring system of the kaurene type.

Abstract

Some steroidal compounds having a bridged bicyclo [3. 2. 1] octane ring system of the kaurene type were syntheiszed starting from the bridged compound (VIa) of the phyllocladene type by two different routes. The major subject of this work is to convert the bridged system of the phyllocladene type into that of the kaurene tupe. The Wagner-Meerwein type rearrangement was successfully applied for this purpose as exemplified by the coversions XVd-XIV and XXII-XXIII. The allylic alcohol function was also successfully introduced into the bridged five-membered ring.