Abstract:We have developed a novel synthetic method to furnish spiroA C H T U N G T R E N N U N G [4.5]cyclohexadienones using an gold-catalyzed carbocyclization of phenols with a terminal alkyne via an intramolecular ipsoFriedel-Crafts alkenylation. Using 2-5 mol% of gold catalyst, 1 equiv. of methanesulfonic acid, and 1 equiv. of 2,6-di-tert-butylpyridine, a variety of spiroA C H T U N G T R E N N U N G [4.5]cyclohexadienone derivatives with an exocyclic olefin unit was obtained in good to excellent yields. The divergent synthesis of dihydronaphthalene derivatives was also examined based on the newly developed gold catalysis.

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A new method to synthesize spiro[4.5]cyclohexadienone derivatives with an exo‐cyclic olefin unit is developed.