Abstract
An effective synthesis of endo-6-bromo-tricyclo[5.2.1.0 2,6]deca-4,8-dien-3-one 3d is realized starting from carboxylic acid 2 applying Barton's halodecarboxylation methodology. Mild basic treatment of 3d leads to quantitative formation of tricyclo[5.2.1.0 2,6]decatrienone 5 which rapidly undergoes either regioselective nucleophilic addition or Diels-Alder cyclization depending on the applied reaction conditions.
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