Journal of Organic Chemistry 2013-02-15

An improved synthesis of (-)-5,11-dideoxytetrodotoxin.

Masaatsu Adachi, Takuya Imazu, Minoru Isobe, Toshio Nishikawa

Index: J. Org. Chem. 78(4) , 1699-705, (2013)

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Abstract

We describe an improved synthesis of (-)-5,11-dideoxytetrodotoxin from an enone, which was used for synthesis of tetrodotoxin and its analogues in this laboratory. One of the major modifications was to establish a two-step guanidinylation of trichloroacetamide of a highly functionalized intermediate, which allowed us to prepare (15)N(2)-labeled 5,11-dideoxytetrodotoxin for biosynthetic investigations.