Sterpurene, a sesquiterpene hydrocarbon metabolite of Chondrostereum purpureum, a plant pathogen and potential mycoherbicide, was synthesized by a six-step sequence, in 33% overall yield. The key steps were a thermal [4+ 2](Diels-Alder) cycloaddition of a ketene acetal diene with a conjugated ester dienophile, and a remarkably stereoselective [2+ 2] photocycloaddition of ethylene with the resulting conjugated ketone. Several related, more ...
