Pyrano[3,4-b]pyrrol-7(1H)-one is a bicyclic structure that is rarely described in the literature but is found in numerous polycyclic natural products as lamellarins. This work presents a one-pot synthesis of pyrano[3,4-b]pyrrol-7(1H)-one substituted in the 2- and 5-position. The reaction proceeds via a one-pot two step 5-endo-dig and 6-endo-dig cyclization catalyzed by a cationic gold complex with high regioselectivity.