title: [Synthetic Studies of Bioactive Heterocyclic Natural Products and Fused Heterocyclic Compounds Based on the Thermal Electrocyclic or Azaelectocyclic Reaction of 6π-Electron or Aza-6π-electron Systems].
abstract: Since 1979, synthetic studies of bioactive heterocyclic natural products and condensed heteroaromatic compounds based on the thermal electrocyclic reaction of 6π-electron or aza-6π-electron systems incorporating the double bond of the principal aromatic or heteroaromatic ring have been conducted by our research group. In this review, five types of electrocyclic and azaelectrocyclic reaction are described: 1) the synthesis of the carbazole alkaloids hyellazole and 6-chlorohyellazole through the electrocyclic reaction of 2,3-bisalkenylindoles; 2) synthetic studies of the pyridocarbazole alkaloids ellipticine and olivacine through the electrocyclic reactions of the indole-2,3- and pyridine-3,4-quinodimethane intermediates; 3) synthetic studies of polysubstituted carbazole alkaloids through the allene-mediated electrocyclic reactions involving the indole 2,3-bond; 4) synthetic studies of fused pyridine rings through the azaelectrocyclic reaction of the 1-aza-6π-electron system using the oxime or oxime ether; and 5) synthetic studies of fused pyridine rings through the azaelectrocyclic reaction of the 2-aza-6π-electron system using a carbodiimide or isocyanate.
authors.affiliation: Graduate School of Pharmacy and Pharmaceutical Sciences, Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University.
authors.forename: Satoshi
authors.initials: S
authors.lastname: Hibino
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry*; D002227:Carbazoles / Q000138:chemical synthesis; D002234:Carbodiimides / Q000737:chemistry; D004583:Electrons; D000072471:Heterocyclic Compounds, Fused-Ring / Q000138:chemical synthesis* / Q000737:chemistry*; D017953:Isocyanates / Q000737:chemistry; D055601:Organic Chemistry Phenomena
chemical_list: D000470:Alkaloids; D001688:Biological Products; D002227:Carbazoles; D002234:Carbodiimides; D000072471:Heterocyclic Compounds, Fused-Ring; D017953:Isocyanates