Exploring Chemical Diversity of Epoxyquinoid Natural Products: Synthesis and Biological Activity of (−)-Jesterone and Related Molecules

Abstract

Enantioselective syntheses of the potent antifungal agent (-)-jesterone, its hydroxy epimer, and a dimeric quinone epoxide derivative are reported. The synthesis involves diastereoselective epoxidation of a chiral quinone monoketal derivative and regio- and stereoselective reduction of a quinone epoxide intermediate.