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.
Leonard
Michael S
MS
Department of Chemistry, Washington & Jefferson College, 60 South Lincoln Street, Washington, Pennsylvania 15301, USA.
Carroll
Patrick J
PJ
Joullié
Madeleine M
MM
D000475:Alkenes / Q000737:chemistry; D031041:Annona / Q000737:chemistry; D001643:Bridged Bicyclo Compounds / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D018360:Crystallography, X-Ray; D004988:Ethers, Cyclic / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D008968:Molecular Conformation; D015394:Molecular Structure; D011108:Polymers / Q000138:chemical synthesis*
D000475:Alkenes; D001643:Bridged Bicyclo Compounds; D004988:Ethers, Cyclic; D007202:Indicators and Reagents; D011108:Polymers; C486108:pondaplin