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

The Journal of organic chemistry (2013-01-18)
Masaatsu Adachi, Takuya Imazu, Minoru Isobe, Toshio Nishikawa
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.

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