Alkaloids with fused polycyclic frameworks are attractive targets for synthetic organic chemists because of their structural complexity and biological activities, and a variety of synthetic strategies have been developed. Herein, we describe our strategy of utilizing oxidative phenolic coupling reaction and regioselective intramolecular aza-Michael reaction to generate fused polycyclic structural frameworks, and its application to total syntheses of (+)-gracilamine and various hasubanan alkaloids.