A novel palladium(II) catalysed tandem cyclisation of substituted 2-alkenylphenyl alkynones gives substituted 2-vinyl indenones and 6,5,6-fused tricyclic lactone skeletons (pyrones), in one-pot. Wagner–Meerwein-like rearrangements were observed which occur preferentially to conventional chloride-mediated chloropalladations of enynes.