A stereoselective synthesis of (-)-tetrodotoxin

J Am Chem Soc. 2003 Sep 24;125(38):11510-1. doi: 10.1021/ja0368305.

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.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Stereoisomerism
  • Tetrodotoxin / chemical synthesis*

Substances

  • Tetrodotoxin