A Concise Synthesis of Tetrodotoxin

Dirk Trauner and Bryan Matsuura present a synthesis of tetrodotoxin, a potent poison found in some fish.

Tetrodotoxin (TTX) is an extremely potent poison found in different organs of some fish, such as puffer fish, as well as in some amphibian, octopus, and shellfish species, acting as a selective sodium channel blocker. Chemically, TTX is a complex quinazoline alkaloid, whose structure was elucidated by Hirata, Tsuda, Amakasu, and Woodward and later confirmed by X-ray crystallography. Its first synthesis – in racemic form – dates back to the work of Yoshito Kishi (1972), whereas the synthesis of the stereopure compound was first accomplished over three decades later. Recently, the group of Professor Dirk Trauner (New York University, USA) reported a conceptually new and extremely concise stereoselective synthesis of TTX, which could also be amenable to readily accessing biologically active TTX derivatives of pharmaceutical interest.

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