Synthesis of a Pondaplin Dimer and Trimer. Aromatic Interactions in Novel Macrocycles

Synthetic challenges in the use of an oxabicyclo[2.2.2]octenone moiety as a masked arene for the synthesis of pondaplin are disclosed. During the course of a study of the Heck reaction as a tool for macrocyclization to provide strained paracyclophanes, novel macrocycles displaying intra- and intermolecular aromatic interactions have been synthesized. The geometry of these interactions is compared to recent computational literature data.