Stereoselective and efficient total synthesis of optically active tetrodotoxin from D-glucose.
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.
Sato
Ken-ichi
K
Department of Applied Chemistry, Faculty of Engineering, Kanagawa University, Yokohama, 221-8686, Japan. satouk01@kanagawa-u.ac.jp
Akai
Shoji
S
Shoji
Hirotsugu
H
Sugita
Naoki
N
Yoshida
Shiho
S
Nagai
Yoshinao
Y
Suzuki
Katsuhiko
K
Nakamura
Yutaka
Y
Kajihara
Yasuhiro
Y
Funabashi
Masuo
M
Yoshimura
Juji
J
D005947:Glucose / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism; D013779:Tetrodotoxin / Q000138:chemical synthesis* / Q000737:chemistry
D013779:Tetrodotoxin; D005947:Glucose