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Herein, we describe a gold(I)-catalyzed generation of nonclassical gold-containing 1,4-all-carbon dipoles from cycloisomerization/1,2-carbene transfer/ring opening cascade reactions of readily accessible allenyl ketones bearing a cyclopropyl moiety and its cyclization with tropone. This method features an unprecedented formal [8+4] high-order cycloaddition under mild conditions for delivering structurally complex 7,7,5-tricycles in generally moderate to high yields.The flexible variation of peptidomimetics is of great in