Enantioselective total synthesis of ( - )-kibdelone C

John R. Butler; Chao Wang; Jianwei Bian; Joseph M. Ready

doi:10.1021/ja204040k

Enantioselective total synthesis of ( - )-kibdelone C

John R. Butler, Chao Wang, Jianwei Bian, Joseph M. Ready

Research output: Contribution to journal › Article › peer-review

67 Scopus citations

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.

Original language	English (US)
Pages (from-to)	9956-9959
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	133
Issue number	26
DOIs	https://doi.org/10.1021/ja204040k
State	Published - Jul 6 2011

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja204040k

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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.",

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AU - Ready, Joseph M.

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AB - 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.

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Enantioselective total synthesis of ( - )-kibdelone C

Abstract

ASJC Scopus subject areas

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