Model Studies in Taxane Diterpene Synthesis. Part III

Abstract

The photocycloaddition of vinyl acetate to enones bearing oxygenated functional groups on their p systems, such as the 1,3 dione enol ether 4a and the 1,3 dione 4b is expected to proceed with high regio and stereoselectivity. The bicyclo [5.2.1] dodecane derivative 3 , an important structural element of simple model taxane diterpenes, was prepared in high yield by the photocycloaddition of enones 4a and 4b to vinyl acetate followed by opening of the thus formed cyclobutane ring, via the de Mayo reaction.