Herein we disclose an unprecedented intramolecular cascade strategy for the construction of α,β-unsaturated [5,5]- and [6,5]-oxaspirolactones that capitalizes on the π-electrophilic Lewis acid-catalyzed 5-exo-dig or 6-exo-dig mode of cyclization of propargylic diol esters, followed by dehydration and spirolactonization steps. Moreover, semi-protected substrates also delivered the respective oxaspirolactones with the same ease and in appreciable yields under optimal reaction conditions.