title: An improved synthesis of (-)-5,11-dideoxytetrodotoxin.
abstract: We describe an improved synthesis of (-)-5,11-dideoxytetrodotoxin from an enone, which was used for synthesis of tetrodotoxin and its analogues in this laboratory. One of the major modifications was to establish a two-step guanidinylation of trichloroacetamide of a highly functionalized intermediate, which allowed us to prepare (15)N(2)-labeled 5,11-dideoxytetrodotoxin for biosynthetic investigations.
authors: Laboratory of Organic Chemistry, Graduate School of Bioagricultural Sciences, Nagoya University, Chikusa, Nagoya 464-8601, Japan.
authors: Masaatsu
authors: M
authors: Adachi
authors: Takuya
authors: T
authors: Imazu
authors: Minoru
authors: M
authors: Isobe
authors: Toshio
authors: T
authors: Nishikawa
mesh_terms: D000081:Acetamides / Q000737:chemistry; D062845:Chloroacetates / Q000737:chemistry; D019791:Guanidine / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013779:Tetrodotoxin / Q000031:analogs & derivatives* / Q000138:chemical synthesis*
chemical_list: D000081:Acetamides; D062845:Chloroacetates; D013779:Tetrodotoxin; C009528:trichloroacetamide; D019791:Guanidine