Merck

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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Guanidine hydrochloride, ≥99.5%
Sigma-Aldrich
Guanidine hydrochloride, BioUltra, for molecular biology, ≥99.5% (AT)
Sigma-Aldrich
Guanidine hydrochloride, ≥99.0% (AT)
Sigma-Aldrich
Guanidine hydrochloride, for molecular biology, ≥99%
Sigma-Aldrich
Guanidine hydrochloride, ≥99% (titration), organic base and chaeotropic agent
Sigma-Aldrich
Guanidine hydrochloride, BioXtra, ≥99.5% (titration)
Sigma-Aldrich
Guanidine hydrochloride, ≥98%
Sigma-Aldrich
Guanidine sulfate salt, 99%
Sigma-Aldrich
Guanidine hydrochloride solution
Sigma-Aldrich
Guanidine hydrochloride solution, BioUltra, ~8 M in H2O