Kathryn A. Punch and Matthew J. Piggott
Org. Biomol. Chem., 2014,12, 2801-2810
DOI:
10.1039/C4OB00331D,
Paper
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.