The Mn(III)-based oxidation of methylenebis(cyclohexanedione)s and methylenebis(piperidinedione)s as a tetracarbonyl compound was investigated under various conditions, selectively producing spiro dihydrofurans and dispiro cyclopropanes depending on the solvent. The mechanism for the formation of the spiro dihydrofurans and dispiro cyclopropanes was discussed. In addition, a simple synthesis of a new type of alkaloid, 3,4,6,7,8,10-hexahydro-1H-pyrano[3,2-c:5,6-c’]dipyridine-1,9(2H)-diones, was demonstrated. © 2020 Elsevier Ltd