title: Synthesis of isoindolobenzazepine alkaloids based on radical reactions or Pd(0)-catalyzed reactions.
abstract: Methods for synthesis of a ring system characteristic of isoindolobenzazepine alkaloids were studied. Synthesis of lennoxamine and a formal synthesis of chelenine were accomplished in a short route via radical or Pd(0)-catalyzed cyclization as the key step. An altenative approach based on a radical migration of a cyano group or Pd(0)-catalyzed carbonylation was also developed for both alkaloids.
authors.affiliation: Laboratory of Organic Synthesis, Division of Molecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan.
authors.forename: Yu
authors.initials: Y
authors.lastname: Onozaki
authors.forename: Nobuhito
authors.initials: N
authors.lastname: Kurono
authors.forename: Hisanori
authors.initials: H
authors.lastname: Senboku
authors.forename: Masao
authors.initials: M
authors.lastname: Tokuda
authors.forename: Kazuhiko
authors.initials: K
authors.lastname: Orito
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001552:Benzazepines / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D005609:Free Radicals / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D001552:Benzazepines; D005609:Free Radicals; D010165:Palladium