CHED 884 |
| Sarah A. Price1, Steve Edwards1, Tiffany Wu2, and Thomas G Minehan1. (1) Department of Chemistry, Harvey Mudd College, 301 East 12th Street, Claremont, CA 91711, (2) Department of Chemistry, Harvard University |
| The goal of this project was to investigate new methods for synthesizing the glycosidic carbon-carbon bond present in naturally occurring C-aryl glycosides using organoindium chemistry. This particular carbon-carbon bond is of interest because these types of compounds have anti-tumor and antibiotic properties and a useful synthesis of them could lift the strain on natural resources. Indium chemistry provides an intriguing choice because organoindium compounds are generally environmentally benign, relatively stable and efficient at transferring all three of their ligands in a coupling reaction. A series of triarylindiums were prepared and allowed to react with 3,4-Di-O-acetyl-6-deoxy-L-glucal, Tri-O-acetyl-D-galactal, and Tri-O-acetyl-D-glucal. The products, which were predominantly α-C-aryl-Δ2,3-glycopyranosides, were purified by column chromatography and characterized by 1H NMR, 13C NMR, IR, 2-dimensional NMR analysis, and TLC. Remarkably, these reactions occur in the absence of a transition-metal catalyst, indicating that triorganoindiums are indeed nucleophilic reagents. |
|
Undergraduate Research Poster Session: Organic Chemistry
2:00 PM-4:00 PM, Monday, March 29, 2004 Anaheim Convention Center -- Hall A, Poster
Division of Chemical Education |