Total synthesis of monosporascone and dihydromonosporascone

Abstract

The first total synthesis of monosporascone is presented. The five-step synthesis developed includes a silver acetylide-acid chloride coupling, domino Diels–Alder-retro-Diels–Alder reaction, and an intramolecular Friedel–Crafts acylation, and provides the natural product in 57% yield overall. Selective reduction of monosporascone also afforded the related metabolite dihydromonosporascone.