title: Total synthesis of (-)-5,6,11-trideoxytetrodotoxin and its 4-epimer.
abstract: [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.
authors.affiliation: Graduate School of Science, Osaka City University, 3-3-138, Sugimoto, Sumiyoshi, Osaka 558-8585, Japan.
authors.forename: Taiki
authors.initials: T
authors.lastname: Umezawa
authors.forename: Toshihiro
authors.initials: T
authors.lastname: Hayashi
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Sakai
authors.forename: Hidetoshi
authors.initials: H
authors.lastname: Teramoto
authors.forename: Takeshi
authors.initials: T
authors.lastname: Yoshikawa
authors.forename: Masashi
authors.initials: M
authors.lastname: Izumida
authors.forename: Yoshinori
authors.initials: Y
authors.lastname: Tamatani
authors.forename: Tadashi
authors.initials: T
authors.lastname: Hirose
authors.forename: Yasufumi
authors.initials: Y
authors.lastname: Ohfune
authors.forename: Tetsuro
authors.initials: T
authors.lastname: Shinada
mesh_terms: D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D013237:Stereoisomerism; D013779:Tetrodotoxin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: C520459:5,6,11-trideoxytetrodotoxin; D009570:Nitriles; C430593:cyanohydrin; D013779:Tetrodotoxin