title: Copper-Catalyzed Annulation: A Method for the Systematic Synthesis of Phenanthridinium Bromide.
abstract: A novel procedure for the Cu-catalyzed systematic synthesis of phenanthridinium bromide is reported. This transformation was achieved with direct construction of central pyridinium core by using an in situ formed biaryl imine as a substrate. Tolerance of a very wide variety of N-substituents is indicated; this has never previously been disclosed by other reports. Application of this method to synthesis of the natural alkaloid bicolorine, and its derivatives, was also carried out in only three synthetic steps from commercially available compounds.
authors.affiliation: Department of Chemistry, Tamkang University , New Taipei City 25137, Taiwan.
authors.forename: Yuan-Ye
authors.initials: YY
authors.lastname: Jhang
authors.affiliation: Department of Chemistry, Tamkang University , New Taipei City 25137, Taiwan.
authors.forename: Tai-Ting
authors.initials: TT
authors.lastname: Fan-Chiang
authors.affiliation: Department of Chemistry, Tamkang University , New Taipei City 25137, Taiwan.
authors.forename: Jun-Min
authors.initials: JM
authors.lastname: Huang
authors.affiliation: Department of Chemistry, Tamkang University , New Taipei City 25137, Taiwan.
authors.forename: Jen-Chieh
authors.initials: JC
authors.lastname: Hsieh
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D006842:Hydrocarbons, Brominated / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010617:Phenanthridines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000470:Alkaloids; D006842:Hydrocarbons, Brominated; D010617:Phenanthridines; C000609064:bicolorine; C014740:phenanthridinium; D003300:Copper; C029892:cupric chloride