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A novel compound bicyclo[3.3.1]nonane-2,6,9-trione was synthesized from cyclohexane-1,3-dione through three routes and some reaction mechanisms were proposed. The first route afforded bicyclo[3.3.1]nonane-2,6,9-trione in a total yield of 43% via Michael addition with cyclohexane-1,3-dione and acrolein, intermolecular Aldol condensation and oxidation. The second route gave target product in 20% yield via a one-pot process including formation of enamine with morpholine and cyclization withdoi:10.6023/cjoc201309009 fatcat:lcawqf6o7bhbhh7gtisvvcctxm