Synthesis of isoindolobenzazepine alkaloids based on radical reactions or Pd(0)-catalyzed reactions.
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.
Onozaki
Yu
Y
Laboratory of Organic Synthesis, Division of Molecular Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo 060-8628, Japan.
Kurono
Nobuhito
N
Senboku
Hisanori
H
Tokuda
Masao
M
Orito
Kazuhiko
K
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
D000470:Alkaloids; D001552:Benzazepines; D005609:Free Radicals; D010165:Palladium