Stereocontrolled synthesis of 8,11-dideoxytetrodotoxin, unnatural analogue of puffer fish toxin.
[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.
Nishikawa
Toshio
T
Laboratory of Organic Chemistry, Graduate School of Bioagricultural Sciences, Nagoya University, Chikusa, Japan.
Urabe
Daisuke
D
Yoshida
Kazumasa
K
Iwabuchi
Tomoko
T
Asai
Masanori
M
Isobe
Minoru
M
D013237:Stereoisomerism; D023721:Tetraodontiformes; D013779:Tetrodotoxin / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry
C465250:8,11-dideoxytetrodotoxin; D013779:Tetrodotoxin