Oxidation of the diols with PCC to the corresponding cyclic diketones 23 and 29, followed by palladium-catalyzed reduction, afforded [14]-and [15] orthocyclophanes, 4 and 5. Bicyclic biscyclophanes were also prepared from the cyclic diketones giving rise to a new family of cyclophanes. Treatment of 23 and 29, respectively, with McMurry or Clemmensen reagents gave rise to intramolecular olefination to provide bicyclic biscyclophanes 24 and 30. Pd- ...
