Herein, we describe a Pd-catalyzed [2+3] cycloaddition/cross-coupling reaction of allenyl acetates for the Z/E selective and diastereoselective synthesis of dendralene-functionalized dihydrofurans. Remarkably, mechanistic studies show the formation of an epoxide from a carbonyl bond via cycloaddition, which is practically and mechanistically significant for the construction of other bioactive heterocyclic epoxides. This research also revealed the utility and potential of allenic esters as C2 synthons and 1,2-biselectrophiles in cycloaddition reactions.