| Summary: | The preparation of unprecedented 6,12-disubstituted methanodibenzo[<i>b</i>,<i>f</i>][1,5]dioxocins from pyrrolidine catalyzed self-condensation of 2′-hydroxyacetophenones is herein described. This method provides easy access to this highly bridged complex core, resulting in construction of two C–O and two C–C bonds, a methylene bridge and two quaternary centers in a single step. The intricate methanodibenzo[<i>b</i>,<i>f</i>][1,5]dioxocin compounds were obtained in up to moderate yields after optimization of the reaction conditions concerning solvent, reaction times and the use of additives. Several halide substituted methanodibenzo[<i>b</i>,<i>f</i>][1,5]dioxocins could be prepared from correspondent 2′-hydroxyacetophenones.
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