A facile and diversity-oriented access to complex tetracyclic benzo[e]pyrrolo[2,3-c]indole-2,4,7(5H)-triones through a post-Ugi gold(i)-catalyzed domino dearomatization/ipso-cyclization/aza-Michael sequence is elaborated. This process furnishes tetracyclic scaffolds in good yields from readily available precursors with unique diastereoselectivity.