Synthesis of a tetraketone bearing a 20-carbon framework represented on the surface of C60

ORGN 769

Hu Cui, chu1@mix.wvu.edu, Jeffrey L. Petersen, and Kung K. Wang. C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506-6045
Tetraketone 4 possessing a 20-carbon framework represented on the surface of C60 was synthesized from 4-bromo-1-indanone. The synthetic route involved a Cu-promoted coupling reaction to form 1 followed by two Pd-catalyzed carboethoxylation reactions to give 2. A subsequent intramolecular Claisen condensation reaction of 2 gave 3, which on treatment with TBAF and iodomethane then led to 4. The structure of 4 was established by X-ray structure analysis, showing a bowl-shaped configuration.