A Total Synthesis of Xestodecalactone A and Proof of Its Absolute Stereochemistry: Interesting Observations on Dienophilic Control with 1,3-Disubstituted Nonequivalent Allenes

Abstract

A concise total synthesis of xestodecalactone A, utilizing a Diels-Alder strategy is described. The focal Diels-Alder reaction relied on an "ynoate" dienophile to rapidly assemble the required resorcylinic acid scaffold. During this study, Diels-Alder cycloaddition reactions involving 1,3-disubstituted nonequivalent allene dienophiles were studied, and some surprising results were encountered.