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Enantioselective Total Synthesis of (+)-Gigantecin: Exploiting the Asymmetric Glycolate Aldol Reaction

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Michael T. Crimmins* and Jin She

Department of Chemistry, Venable and Kenan Laboratories of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3290

J. Am. Chem. Soc., 2004, 126 (40), pp 12790–12791

DOI: 10.1021/ja0455852

Publication Date (Web): September 18, 2004

Abstract

The enantioselective synthesis of the potent, selective, cytotoxic, annonaceous acetogenin, (+)-gigantecin, has been completed. An asymmetric glycolate aldol serves to establish the stereocenters at C13,14 and at C21,22. A Carreira asymmetric acetylide addition is used to establish the C17 stereocenter.

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Published In Issue October 13, 2004
Received July 22, 2004

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Communication

Enantioselective Total Synthesis of (+)-Gigantecin: Exploiting the Asymmetric Glycolate Aldol Reaction

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Total Syntheses of Isodomoic Acids G and H: An Exercise in Tetrasubstituted Alkene Synthesis

Synthesis of Dialkyl Ethers from Organotrifluoroborates and Acetals

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