ORGN 82 |
| Gagik G. Melikyan, Arthur Florut, and Christopher Wild. Department of Chemistry, California State University Northridge, 18111 Nordhoff str, Northridge, CA 91330 |
| Novel radical C-C bond forming reactions – spontaneous and THF-mediated dimerization of cobalt-complexed propargyl systems (Org.Lett. 2003, 5, 3395; J.Organomet.Chem. 2003, 683, 324) – were used, as a key step, in the stereoselective assembling of novel nonsteroidal hormones. The topology of polyphenolic structures having a D,L-3,4-disubstituted 1,5-hexadiyne backbone was designed based on the anticipated biological activity and the most conceivable metabolic pathways. The typical synthetic scheme includes the preparation of dicobalthexacarbonyl-propargyl alcohol complex, followed by the generation of carbocationic and radical centers in alpha-position to the metal core. The efficacy of radical coupling reactions is found to be dependent upon the substrate structure and an electronic nature, disposition and a number of substituents at aromatic nuclei. The intramolecular variant of the parent reaction will also be presented, along with the preliminary data on antiestrogenic activity of lead compounds. |
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New Reactions and Methodology, Metal-Mediated Reactions, Heterocycles and Aromatics
8:00 PM-10:00 PM, Sunday, March 28, 2004 Anaheim Convention Center -- Hall A, Poster
Division of Organic Chemistry |