J Am Chem Soc. 2003 Sep 24;125(38):11510-1.

A stereoselective synthesis of (-)-tetrodotoxin.

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

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.

PMID:: 13129349; [PubMed - indexed for MEDLINE]

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Tetrodotoxin

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