Abstract
| - 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 variousacrylates followed by manipulation of the resulting tricyclic adducts, leading to functionalized tricyclo[5.2.2.01,5]undecenones and tricyclo[6.2.2.01,6]dodecenones endowed with a β,γ-enone chromophore.Photochemical reaction of the tricyclic chromophoric systems followed by reductive cleavage providedan efficient entry into propellanes.
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