A diene-transmissive approach to the quassinoid skeleton

Abstract

Several tetracyclic molecules were prepared by diene-transmissive Diels–Alder cycloadditions. Control over the stereochemical outcome of the cycloaddition was achieved and the structural features of the precursors affecting the stereochemistry is discussed. Useful information was gathered concerning the factors governing this stereocontrol, which will be indispensable for the future of this strategy.Key words: quassinoid, anticancer agent, diene-transmissive Diels–Alder cycloaddition, oxadiene, hetero Diels–Alder.