Synthesis of pyrone-annulated 2-oxabicyclo[3.3.1]nonanes by palladium-catalyzed cyclization of 4-hydroxy-2-pyrones with allylic bisacetates

[Display omitted] •A Pd-catalyzed reaction of 4-hydroxy-2-pyrones with 1,4-diacetoxy-2-cyclohexene.•A pyrone-annulated 2-oxabicyclo[3.3.1]nonane scaffold has been constructed.•Furo[3,2-c]pyranone was produced by decreasing the reaction temperature. Cyclization of 4-hydroxy-2-pyrones with allylic bisacetates by a palladium catalyst is described. Pyrone-annulated 2-oxabicyclo[3.3.1]nonane derivatives were regioselectively produced from the reaction of 4-hydroxy-2-pyrones with 1,4-diacetoxy-2-cyclohexene at high temperature. The reaction would proceed via a migration of the π-allylpalladium intermediate.