An Efficient Total Synthesis of Optically Active Tetrodotoxin

2004/09/07 by Toshio Nishikawa, Daisuke Urabe, Minoru Isobe · 4 citations
Environmental Science · Chemistry · Pharmacology, Toxicology and Pharmaceutics · #Marine Toxins and Detection Methods #Chemical synthesis and alkaloids #Alkaloids: synthesis and pharmacology

paper · doi:10.1002/anie.200460293

openalex publication_date 2004/09/07 · openalex created_date 2025/10/10 · openalex updated_date 2026/07/25

Abstract

The toxic principle of puffer-fish poison, (−)-tetrodotoxin (1), has been recognized as a formidable synthetic target since its structure elucidation in 1964. An efficient total synthesis of 1 via the intermediate 2, which was used previously for the synthesis of 11-deoxytetrodotoxin, is described.

Citations

• Synthetic studies on tetrodotoxin and related compounds. III. Stereospecific synthesis of an equivalent of acetylated tetrodamine
• Synthetic studies on tetrodotoxin and related compounds. IV. Stereospecific total syntheses of DL-tetrodotoxin
• The structure of tetrodotoxin
• Tetrodotoxin Blockage of Sodium Conductance Increase in Lobster Giant Axons

Cited by

• The Chemical Synthesis of Tetrodoxin: An Ongoing Quest
• 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]