Exploring chemical diversity of epoxyquinoid natural products: synthesis and biological activity of (-)-jesterone and related molecules.

Org Lett

Department of Chemistry, Metcalf Center for Science and Engineering, Boston University, 590 Commonwealth Avenue, Boston, MA 02215, USA.

Published: May 2001

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.

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http://dx.doi.org/10.1021/ol0159367DOI Listing

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