A general stereoselective route to functionalized and substituted tricyclo [5.2. 2.01, 5] undecenones, tricyclo [6.2. 2.01, 6] dodecenones, and [3.3. 3]-and [4.3. 3] propellanes from simple aromatic precursors is reported. The methodology involves generation and cycloaddition of annulated cyclohexa-2, 4-dienones with various acrylates followed by manipulation of the resulting tricyclic adducts, leading to functionalized tricyclo [5.2. 2.01, ...