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Synthesis of Tetrodotoxin, a Classic but Still Fascinating Natural Product
Author(s) -
Nishikawa Toshio,
Isobe Minoru
Publication year - 2013
Publication title -
the chemical record
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.61
H-Index - 78
eISSN - 1528-0691
pISSN - 1527-8999
DOI - 10.1002/tcr.201200025
Subject(s) - tetrodotoxin , natural product , fish <actinopterygii> , chemistry , nanotechnology , biochemical engineering , biology , fishery , biophysics , biochemistry , materials science , engineering
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.