A Total Synthesis of Xestodecalactone A and Proof of Its Absolute Stereochemistry: Interesting Observations on Dienophilic Control with 1,3-Disubstituted Nonequivalent Allenes
Journal of the American Chemical Society2006Vol. 128(43), pp. 14185–14191
Citations Over TimeTop 19% of 2006 papers
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.
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