A Radical Cyclization Approach to Isoindolobenzazepines. Synthesis of Lennoxamine.
The alkaloid lennoxamine (1) was synthesized by transannular cyclization of a 10-membered lactam obtained by intramolecular addition of an aryl radical to a (trimethylsilyl)acetylene. The isoindolo[1,2-b][3]benzazepine skeleton present in lennoxamine was also obtained by means of regioselective 7-endo-trig radical cyclization of methylenephthalimidines.
Rodríguez
Gema
G
Departamento de Química Orgánica, Facultad de Química, Universidad de Santiago y Sección de Alcaloides del C. S. I. C. 15706 Santiago, Spain.
Cid
M. Magdalena
MM
Saá
Carlos
C
Castedo
Luis
L
Domínguez
Domingo
D