Synthesis based on cyclohexadienes. Part 24.1 A new total synthesis of pupukean-2-one and a facile entry to copa and ylanga type sesquiterpene skeletons

Abstract

A novel tandem 5-exo-trig allyl and 3-exo-trig radical cyclisation and rearrangement to copa and ylanga type sesquiterpene skeletons from easily prepared cyclohexadienes is reported. A new total synthesis of pupukean-2-one 8, which belongs to a novel class of sesquiterpenes, involving a 5-exo-trig allyl radical cyclisation as the key step is also reported.