Synthesis of a Novel, Highly Symmetric Bis-Oxa-Bridged Compound

A highly oxygenated, novel pentacyclic bis-oxa-bridged compound 8 was synthesized with remarkable efficiency starting from readily available tetrachloro-5,5-dimethoxyclopentadiene and 1,4-cyclohexadiene in three steps. The ruthenium-catalyzed oxidation of 2:1 bis-adduct 1 followed by a one-pot transformation of the resulting bis-α-diketone 3 furnished (after esterification) the title compound in an overall yield of 29.1%. The versatility of this simple method was further demonstrated with other norbornyl α-diketones to obtain the corresponding strained oxa-bridged derivatives.