Lamellarins are polycyclic marine alkaloids with potent cytotoxic activities against cancer cell lines. A divergent synthesis of azalamellarins D and N, lactam congeners of the marine natural products lamellarins D and N, has been achieved via the pentacyclic 14-bromo-8,9-dihydro-benzo[7,8]indolizino[3,2-c]quinolin-6(5H)-one intermediate. The pentacyclic intermediate can be synthesized from methyl 1-(benzensulfonyl)-3-bromo-1H-pyrrole-2-carboxylate via the Suzuki-Miyaura cross-coupling and intramolecular direct arylation as key reactions.