A novel synthetic approach to isoindolobenzazepine alkaloid, chilenine, employing SmI2-mediated pinacolic coupling reaction

Samarium(II) diiodide-mediated intramolecular reductive coupling reaction of phthalimides with N-formylated alkyl side chains is shown to afford dihydroxylated tricyclic lactams with 5–7-membered rings. This process was further applied for the preparation of an isoindolobenzazepine alkaloid, chilenine, by featuring the elaboration of the functionalized phthalimide derivative.