title: Synthesis of tetrodotoxin, a classic but still fascinating natural product.
abstract: Tetrodotoxin, a toxic principle of puffer fish intoxication, is one of the most famous marine natural products due to its densely functionalized structure and potent toxicity. Despite its small molecular size (MW 319 g mol⁻¹), tetrodotoxin has long been well known as a formidable molecule in natural product synthesis. We have devoted more than twenty years to developing synthetic strategies for this molecule, resulting in the preparation of a variety of analogues of tetrodotoxin for biological experiments. This account describes a brief history of tetrodotoxin research and an overview of our synthetic efforts toward tetrodotoxin with the underlying logic and strategy.
authors: Graduate School of Bioagricultural Sciences, Nagoya University, Chikusa, Nagoya, Japan. nisikawa@agr.nagoya-u.ac.jp
authors: Toshio
authors: T
authors: Nishikawa
authors: Minoru
authors: M
authors: Isobe
mesh_terms: D000818:Animals; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D061565:Cycloaddition Reaction; D003510:Cyclohexanes / Q000737:chemistry; D019791:Guanidine / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry; D008958:Models, Molecular; D013237:Stereoisomerism; D023721:Tetraodontiformes / Q000378:metabolism; D013779:Tetrodotoxin / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001688:Biological Products; D003510:Cyclohexanes; D007783:Lactones; D013779:Tetrodotoxin; C506365:Cyclohexane; D019791:Guanidine