Abstract
An effective synthesis of 6-functionalized endo-tricyclo[5.2.1.0 2,6]deca-4,8-dien-3-ones 7 starting from carboxylic acid 6 has been accomplished whereby the chemical scope of the tricyclodecadienone system 1 as a synthetic equivalent of cyclopentadienone has been expanded. Bridgehead bromide 7d gives upon treatment with base access to norbornene annulated cyclopentadienone 10 which rapidly undergoes either regioselective nucleophilic addition or Diels-Alder cyclization depending on the applied reaction conditions.
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