Cascade aza-Piancatelli reaction and [3 + 3]/[4 + 2] cycloaddition reactions are carried out using the ideality principles of pot, atom, and step economy (PASE) synthesis. The reaction resulted in generation of octahydro-4H-cyclopenta[b]pyridin-6-one scaf-folds. Moreover, octahydro-5,7a-epoxycyclopenta [cd]isoindol-4one frameworks of gracilamine alkaloid and a novel decahydro-1H-dicyclopenta [cd,hi]isoindol-6-one were also realized in good yields with excellent regio-and diastereo-selectivities.