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Communication

A Stereoselective Synthesis of (−)-Tetrodotoxin

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Andrew Hinman and J. Du Bois*

Department of Chemistry, Stanford University, Stanford, California 94305-5080

J. Am. Chem. Soc., 2003, 125 (38), pp 11510–11511

DOI: 10.1021/ja0368305

Publication Date (Web): August 30, 2003

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

, jdubois@stanford.edu

Abstract

An asymmetric synthesis of the fugu fish poison, (−)-tetrodotoxin, is described. The route to this extraordinary target employs a number of unique transformations, foremost of which are two stereospecific C−H bond functionalization reactions. Accordingly, Rh-catalyzed carbene and nitrene C−H insertions facilitate rapid entry to the cyclohexane core of the natural product and make possible the late-stage installation of the tetrasubstituted carbinolamine center.

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Published In Issue September 24, 2003
Received June 22, 2003

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Communication

A Stereoselective Synthesis of (−)-Tetrodotoxin

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Expanding the Scope of C−H Amination through Catalyst Design

Synthesis of 1,3-Difunctionalized Amine Derivatives through Selective C−H Bond Oxidation

A Synthesis of (+)-Saxitoxin

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