Stereocontrolled synthesis of 8,11-dideoxytetrodotoxin, unnatural analogue of puffer fish toxin

Toshio Nishikawa; Daisuke Urabe; Kazumasa Yoshida; Tomoko Iwabuchi; Masanori Asai; Minoru Isobe

doi:10.1021/ol026177a

Stereocontrolled synthesis of 8,11-dideoxytetrodotoxin, unnatural analogue of puffer fish toxin

Org Lett. 2002 Aug 8;4(16):2679-82. doi: 10.1021/ol026177a.

Authors

Toshio Nishikawa¹, Daisuke Urabe, Kazumasa Yoshida, Tomoko Iwabuchi, Masanori Asai, Minoru Isobe

Affiliation

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

PMID: 12153208
DOI: 10.1021/ol026177a

Abstract

[structure: see text] 8,11-Dideoxytetrodotoxin, an unnatural tetrodotoxin analogue, was synthesized in a highly stereoselective manner from a common intermediate in our synthetic studies on tetrodotoxin. The synthesis features neighboring group participation of trichloroacetamide for stereoselective hydroxylation, protection of ortho ester, and guanidine installation with Boc-protected isothiourea.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Stereoisomerism
Tetraodontiformes
Tetrodotoxin / analogs & derivatives*
Tetrodotoxin / chemical synthesis*
Tetrodotoxin / chemistry

Substances

8,11-dideoxytetrodotoxin
Tetrodotoxin