Synthesis of a novel, highly symmetric bis-oxa-bridged compound
Faiz Ahmed Khan1, Jyotirmayee Dash
1Department of Chemistry, Indian Institute of Technology, Kanpur-208 016, India.
Abstract:
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-alpha-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 alpha-diketones to obtain the corresponding strained oxa-bridged derivatives.
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