Inspired by the chemistry and biology of chromone, a method for the construction of spirooxindole-based tetrahydrocyclopenta[b]chromanones is reported with good regio-and diastereoselectivity (all cases > 20:1 dr) and moderate yields (up to 67%). This method leads to the construction of four contiguous stereogenic tertiary centers and one spiro quaternary center via a one-step γ-regioselective cascade [3 + 2] cycloaddition of an oxindole-chromone synthon with 3-methyl-4-nitro-5-alkenyl-isoxazole.