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Communication

Total Synthesis of Brasoside and Littoralisone

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Ian K. Mangion and David W. C. MacMillan*

Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125

J. Am. Chem. Soc., 2005, 127 (11), pp 3696–3697

DOI: 10.1021/ja050064f

Publication Date (Web): February 26, 2005

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, Dmacmill@caltech.edu

Abstract

The first total syntheses of littoralisone (1) and brasoside (2) have been achieved in 13 overall steps. Both natural products are forged from a common intermediate which is rapidly assembled using organocatalytic technology, including a proline-catalyzed α-aminoxylation and a contra-thermodynamic intramolecular Michael addition. Application of the two-step carbohydrate synthesis technology has enabled to access a selectively substituted glucose derivative for use as an intramolecular cycloaddition tether. This synthesis culminates with an intramolecular [2+2] photocycloaddition that serves to support the proposed biosynthetic origins of 1 from 2.

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Published In Issue March 23, 2005
Received January 5, 2005

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Communication

Total Synthesis of Brasoside and Littoralisone

Abstract

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SciFinder Links

History

Recommend & Share

Related Content

Enantioselective Organo-Cascade Catalysis

The Direct and Enantioselective Organocatalytic α-Oxidation of Aldehydes

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