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