Work

Stereocontrolled Synthesis of 8,11‐Dideoxytetrodotoxin, An Unnatural Analogue of Puffer Fish Toxin

Year: 2004

Type: article

Abstract: 8,11-Dideoxytetrodotoxin, an unnatural tetrodotoxin analogue, was synthesized in a highly stereoselective manner from a common intermediate from our synthetic studies on tetrodotoxin. The key features in the synthesis were as follows: neighboring group participation of a trichloroacetamide to allow regioselective and stereoselective hydroxylation, protection of a delta-hydroxylactone as an ortho ester, and guanidine installation through the use of Boc-protected isothiourea. Global deprotection of the fully protected intermediate under acidic conditions gave 8,11-dideoxytetrodotoxin, which exhibited very weak biological activities.

Source: Chemistry - A European Journal

DOI: 10.1002/chem.200305111

Authors: Toshio Nishikawa, Daisuke Urabe, Kazumasa Yoshida, Tomoko Iwabuchi, Masanori Asai, Minoru Isobe

Institution: Nagoya University

Language: English

Topic: Advanced Synthetic Organic Chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: bronze

Funders: Pfizer, Japan Science and Technology Corporation, Japan Society for the Promotion of Science, Precursory Research for Embryonic Science and Technology

OpenAlex ID: W2042948764

FWCI: 1.214

Cites: 47

Cited by: 38

Related to: 10