Ag old (I)-catalyzed reactiono fe nyne-etherst o rapidly construct oxa-bridged compoundsv ia at andem 1,2-acyloxy migration/intramolecularo xonium formation/ 1,2-rearrangement process was reported. The reaction was shown to be robust with aw ide range of substitution patterns tolerated to provide the corresponding oxygen-containing bridged products in good to excellent yields.Developing general and efficient methods for the construction of structurally diverse and complex polycyclic skeletons is important for natural products synthesis and lead discovery. [1] Oxygen-bridged bicyclic skeletons are ubiquitous structures in aw ide range of synthetic andn atural products, [2] such as Balsamiferine J, [2h] Englerin B, [2e] WaltherioneC, [2f] Mollanol A, [2g] Coutistatin A [2k] (Scheme 1). Highlye fficient construction of these oxa-bridged skeletons is one of the most important themes in organic synthesis. Much effort hasbeen made to de-Scheme1.Representative natural products with oxa-bridged bicyclic skeletons.Scheme2.Proposed gold-catalyzed propargyle ster rearrangements and further transformations.