Total Synthesis of Tetrodotoxin.

A total synthesis of tetrodotoxin was accomplished. A Diels-Alder reaction between a known enone and a siloxy diene gave a tricyclic product, the steric bias of which was used to construct the remaining stereogenic centers. A nitrogen atom was introduced either by a four-step sequence involving a Curtius rearrangement, or a three-step sequence featuring a newly developed transformation of a terminal alkyne into a nitrile. Introduction of the guanidine moiety followed by the formation of the heterocyclic system by cascade reactions led to tetrodotoxin. © 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Citation

Keigo Murakami, Tatsuya Toma, Tohru Fukuyama, Satoshi Yokoshima. Total Synthesis of Tetrodotoxin. Angewandte Chemie (International ed. in English). 2020 Apr 06;59(15):6253-6257

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PMID: 31985136

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