SYNTHETIC STUDIES ON PLAKINIDINES

Synthetic studies on plakinidines are described. As a model study for the construction of the dihydropyridone ring at the final stage of the synthesis, we investigated a Meyer-Schuster rearrangement/aza-Michael cyclization cascade. The B,C,D,E ring system possessing a pyrrolo[2,3,4-kl]acridine structure was constructed via a benzyne-mediated cyclization/functionalization sequence that involved the formation of a beta,beta-diarylethylamine derivative and a palladium-catalyzed double aryl amination of a 3-arylindoline intermediate as key processes.