ORGN 280 |
| Two different but somewhat related strategies for the synthesis of complex heterocycles that have been developed by this laboratory were put to test for the construction of the skeleton of catharanthine, an important member of the iboga class of alkaloids and a well known precursor of the anticancer agents vinblastine and vincristine. The key step in one approach is based on an intramolecular Diels-Alder cycloaddition between an amido furan and a tethered indolyl dienophile. The other approach is based on a push-pull dipole formed by exposure of a diazo imide precursor to a rhodium(II) catalyst followed by a subsequent [3+2]-cycloaddition across the tethered dipolarophile. This presentation will outline our early model studies as well as some additional applications of the method toward related alkaloids.
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Total Synthesis of Complex Molecules
8:00 AM-12:00 PM, Monday, 14 March 2005 Convention Center -- Room 10, Oral
Division of Organic Chemistry |
