The treatment of readily available propargylic indole-3-acetates with a catalytic amount of AuCl (PPh3)/AgSbF6 leads to tandem activations of the propargylic esters and the in situ generated allenylic esters, resulting in expeditious access to highly functionalized cyclobutanes with fused 2, 3-indoline and γ-lactone rings and an exocyclic E-double bond through sequential 3, 3-rearrangement and [2+ 2] cyclization.