Synthesis of substituted [3]dendralenes and their unique cycloaddition reactions

Abstract

Dimethylsulfonium methylide mediated olefination of 2-phenylethenylidene phosphonoacetate followed by the Horner–Wadsworth–Emmons reaction with aromatic aldehydes provided access to reactive 1,5-diaryl-2-ethoxycarbonyl [3]dendralenes which in situ underwent Diels–Alder cyclodimerisation leading to highly functionalised cyclohexenes with very high regio- and stereoselectivity.