One-Pot Synthesis of Benzo[c]phenanthridine Alkaloids from 7-Azabenzonorbornadienes and Aryl Nitrones

An efficient synthesis of benzo-[c]-phenanthridinealkaloids via a synergistic combination of C-C bond formationand a cycloaromatization reaction is described. Aryl nitrones reactwith 7-azabenzonorbornadienes in the presence of a Rh-(III) catalyst,providing pharmaceutically useful benzo-[c]-phenanthridinederivatives in good to moderate yields. Using this methodology, highlyuseful alkaloids such as norfagaronine, norchelerythrine, decarine,norsanguinarine, and nornitidine were prepared in a single step.

Automated summary

An efficient synthesis of benzo-[c]-phenanthridine alkaloids via a synergistic combination of C-C bond formation and a cycloaromatization reaction is described. Aryl nitrones react with 7-azabenzonorbornadienes in the presence of a Rh-(III) catalyst, providing pharmaceutically useful benzo-[c]-phenanthridine derivatives in good to moderate yields. Using this methodology, highly useful alkaloids such as norfagaronine, norchelerythrine, decarine, norsanguinarine, and nornitidine were prepared in a single step.