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. This journal is © the Partner Organisations 2014.