A Stereoselective Synthesis of (−)-Tetrodotoxin

2003/08/30 by A. Scott Hinman, J. Du Bois · 3 citations
Chemistry · #Synthesis and Catalytic Reactions #Catalytic C–H Functionalization Methods #Synthetic Organic Chemistry Methods

paper · doi:10.1021/ja0368305

openalex publication_date 2003/08/30 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/17

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.

Citations

• First Asymmetric Total Synthesis of Tetrodotoxin
• Synthetic studies on tetrodotoxin and related compounds. IV. Stereospecific total syntheses of DL-tetrodotoxin
• Tarichatoxin—Tetrodotoxin: A Potent Neurotoxin
• The structure of tetrodotoxin

Cited by

• Tetrodotoxin: Chemistry, Toxicity, Source, Distribution and Detection
• Stereocontrolled Total Synthesis of Tetrodotoxin from myo- Inositol and D-Glucose by Three Routes: Aspects for Constructing Complex Multi-Functionalized Cyclitols with Branched-Chain Structures
• Tetrodotoxin [wikipedia]