A novel and selective synthesis of polycyclic fused maleimides from easily available raw materials under metal-free conditions is presented. This cascade protocol involves self-condensation of cyclohexanones, followed by Diels-Alder reaction with maleimides, intramolecular dehydration, and selective dehydroaromatization in a one-pot fashion, affording maleimide-fused 9,10-phenanthrenes and their analogues in satisfactory yields. Notably, iodide reagents play a critical role in switching the selectivity toward full or partial dehydrogenation compounds.