title: Stereoselective and efficient total synthesis of optically active tetrodotoxin from D-glucose.
abstract: A stereoselective and efficient total synthesis of optically active tetrodotoxin (TTX) is described. A polyfunctionalized key cyclitol compound containing branched-chains for the synthesis of TTX was prepared from D-glucose employing the Henry reaction (Nitro aldol reaction) as the key transformation. Stereoselective construction of the alpha-azido-aldehyde branched-chain was achieved via the key spiro alpha-chloroepoxide intermediate.
authors.affiliation: Department of Applied Chemistry, Faculty of Engineering, Kanagawa University, Yokohama, 221-8686, Japan. satouk01@kanagawa-u.ac.jp
authors.forename: Ken-ichi
authors.initials: K
authors.lastname: Sato
authors.forename: Shoji
authors.initials: S
authors.lastname: Akai
authors.forename: Hirotsugu
authors.initials: H
authors.lastname: Shoji
authors.forename: Naoki
authors.initials: N
authors.lastname: Sugita
authors.forename: Shiho
authors.initials: S
authors.lastname: Yoshida
authors.forename: Yoshinao
authors.initials: Y
authors.lastname: Nagai
authors.forename: Katsuhiko
authors.initials: K
authors.lastname: Suzuki
authors.forename: Yutaka
authors.initials: Y
authors.lastname: Nakamura
authors.forename: Yasuhiro
authors.initials: Y
authors.lastname: Kajihara
authors.forename: Masuo
authors.initials: M
authors.lastname: Funabashi
authors.forename: Juji
authors.initials: J
authors.lastname: Yoshimura
mesh_terms: D005947:Glucose / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism; D013779:Tetrodotoxin / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D013779:Tetrodotoxin; D005947:Glucose