Our [3+2]heteroannulation strategy was extended to the targeted synthesis of biologically-active tetracyclic carbazoles. Carbazole-1,4-quinones (e.g., 21a-f) have established anti-cancer activity via topoisomerase inhibition or by the production of reactive oxygen species. We used 21b as a key intermediary scaffold for the targeted synthesis of a deaza analogue of the natural product 9-methoxyellipticine (Scheme 3b), producing 24 in 3 steps and in an overall yield of 20%. Further exemplification of our strategy was demonstrated by the preparation of alkylated 7H-pyridocarbazoles (e.g. 9a-e) which have well-established anti-cancer activity. Previous preparative methods of this series of compounds have involved a 6-step linear synthesis affording compound 9e in 28% overall yield. Our two-step convergent strategy accessed the 7H-pyrido [4,3-c]carbazole core 9e in a single step (83%), followed by alkylation to produce mono-N-alkylated examples (25-26), and the potent anti-cancer agent ditercalinium (27). In summary, we have established a mechanistic framework for the preparation of fused tetracyclic carbazoles. We envisage that this convergent approach could find application in medicinal chemistry for structure-activity profiling and in broader synthetic applications which require step-efficient access to carbazole scaffolds.