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Stereocontrolled Synthesis of 8,11‐Dideoxytetrodotoxin, An Unnatural Analogue of Puffer Fish Toxin
Author(s) -
Nishikawa Toshio,
Urabe Daisuke,
Yoshida Kazumasa,
Iwabuchi Tomoko,
Asai Masanori,
Isobe Minoru
Publication year - 2004
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200305111
Subject(s) - stereoselectivity , tetrodotoxin , regioselectivity , hydroxylation , guanidine , chemistry , toxin , stereochemistry , combinatorial chemistry , biochemistry , biology , enzyme , catalysis , biophysics
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 δ‐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.