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J Am Chem Soc. 2011 Jul 6;133(26):9956-9. doi: 10.1021/ja204040k. Epub 2011 Jun 15.

Enantioselective total synthesis of (-)-kibdelone C.

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  • 1Department of Biochemistry, University of Texas Southwestern Medical Center, 5323 Harry Hines Boulevard, Dallas, Texas 75390-9038, USA.

Abstract

The kibdelones are aromatic polyketide natural products featuring isoquinolinone and tetrahydroxanthone ring systems. They display potent cytotoxicity toward a range of human cancer cell lines. Here, we present an enantioselective total synthesis of kibdelone C that utilizes a Shi epoxidation to establish the absolute and relative stereochemistry, an acid-catalyzed cyclization to form the tetrahydroxanthone, and a C-H arylation to complete the hexacyclic skeleton.

PMID:
21648478
[PubMed - indexed for MEDLINE]
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