Total synthesis of (-)-5,6,11-trideoxytetrodotoxin and its 4-epimer.
[reaction: see text] The first total synthesis of 5,6,11-trideoxytetrodotoxin (1) and its 4-epimer were achieved. The synthesis is characterized by the stereoselective construction of the quaternary amino carbon center at C8a by an asymmetric transferring Strecker synthesis and the highly efficient conversion of cyanohydrin 4 to 1 via intramolecular cyclization reactions.
Umezawa
Taiki
T
Graduate School of Science, Osaka City University, 3-3-138, Sugimoto, Sumiyoshi, Osaka 558-8585, Japan.
Hayashi
Toshihiro
T
Sakai
Hiroshi
H
Teramoto
Hidetoshi
H
Yoshikawa
Takeshi
T
Izumida
Masashi
M
Tamatani
Yoshinori
Y
Hirose
Tadashi
T
Ohfune
Yasufumi
Y
Shinada
Tetsuro
T
D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D013237:Stereoisomerism; D013779:Tetrodotoxin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
C520459:5,6,11-trideoxytetrodotoxin; D009570:Nitriles; C430593:cyanohydrin; D013779:Tetrodotoxin