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Polyene cyclizations are one of the most powerful and fascinating chemical transformations to rapidly generate molecular complexity. However, cyclizations employing heteroatom-substituted polyenes are rare. Herein, we describe the tetracyclization of a dual nucleophilic aryl enol ether involving an unprecedented transannular endo-termination step. In this transformation, five stereocenters, two of which are quaternary, four carbon-carbon bonds and four six-membered rings are formed from a readily available cyclization precursor. The rea