Herein we report a highly regioselective silver(I)-catalyzed intramolecular annulation of alkyne-tethered cyclohexadienones to access meta-substituted phenols with enone functionality, which are difficult to synthesize from conventional methods. The reaction proceeds via intramolecular 1,6-enyne cyclization followed by aromatization and subsequent oxetene ring rearrangement. This strategy has also been compatible with a wide range of C-tethered cyclohexadienones to afford indanes in high yields. The unique functionality of products allows further transformations to expand the diversity.