Asymmetric Total Synthesis of 11-Deoxytetrodotoxin, a Naturally Occurring Congener

• Published in: Journal of the American Chemical Society Vol. 124; no. 26; pp. 7847 - 7852
• Main Authors: Nishikawa, Toshio, Asai, Masanori, Isobe, Minoru
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 03.07.2002; Amer Chemical Soc
• Subjects: Animal poisons toxicology. Antivenoms; Animals; Biological and medical sciences; Chemistry; Chemistry, Multidisciplinary; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms; Medical sciences; Organic chemistry; Physical Sciences; Preparations and properties; Science & Technology; Tetraodontiformes; Tetrodotoxin - chemical synthesis; Toxicology; TETRODOTOXIN BINDING-PROTEIN; PUFFER FISH; NA+ CHANNEL; (-)-TETRODOTOXIN; CHEMISTRY; FUGU-PARDALIS; SODIUM-CHANNEL; DERIVATIVES; STEREOCONTROLLED SYNTHESIS; STEREOSELECTIVE SYNTHESIS; Toxin; Asymmetric synthesis; Nitrogen heterocycle; Animal origin; Polycyclic compound; Oxygen heterocycle; Total synthesis

Tetrodotoxin, a toxic principle of puffer fish poisoning, is a specific blocker of sodium channel. Despite many synthetic efforts since the structure elucidation in 1964, the only total synthesis of the racemic tetrodotoxin has been reported by Kishi and co-workers. In the course of our studies dire...