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J Org Chem. 2013 Feb 15;78(4):1699-705. doi: 10.1021/jo302773f. Epub 2013 Jan 30.

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

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1
Laboratory of Organic Chemistry, Graduate School of Bioagricultural Sciences, Nagoya University, Chikusa, Nagoya 464-8601, Japan.

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.

PMID:
23323757
DOI:
10.1021/jo302773f
[Indexed for MEDLINE]
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