Total synthesis of (±)-cavicularin: control of pyrone Diels-Alder regiochemistry using isomeric vinyl sulfones.

An intramolecular pyrone Diels-Alder reaction-elimination retro-Diels-Alder cascade of a vinyl sulfone was used in the synthesis of cavicularin, a molecule possessing conformational chirality. The vinyl sulfone substitution pattern allowed for regiocontrol in the Diels-Alder cascade event.