Total Synthesis of (±)-Kuwanol E

Abstract

The total synthesis of the Diels-Alder-type adducts (±)-kuwanol E and the heptamethyl ether derivative of (±)-kuwanon Y has been accomplished via a convergent strategy involving 2'-hydroxychalcone 6 or 9 and dehydroprenylstilbene 7, in nine steps. The synthesis features, as a key step, a Lewis acid-mediated biomimetic intermolecular Diels-Alder [4+2] cycloaddition for the construction of the cyclohexene skeleton with three stereogenic centers. Notably, the endo/exo diastereoselectivity of the reaction proved to be temperature-controlled.