A palladium-catalyzed highly regioselective and chemoselective intermolecular cyclization of 2,7-alkadiynylic carbonates with terminal propargyl tertiary alcohols to construct benzopolycycles containing furan and pyrrole moieties has been developed with a very broad scope. Polycycles containing spirane structures or dispirane structures could be also smoothly synthesized in moderate to good yields. The reaction enjoys excellent regioselectivity.