ORGN 596 |
| Weimin Lin, Cory R. Theberge, and Charles K. Zercher. Department of Chemistry, University of New Hampshire, Durham, NH 03824 |
| A variety of N-protected amino acid derived keto esters have been prepared by a zinc-mediated chain extension reaction in which a single methylene unit is inserted between ester and ketone carbonyls. This method has been applied to amino acids that contain various protective groups and a variety of side chain functionality. Tandem chain extension-zinc enolate reactions were used to generate substituted ketomethylene isosteric amino acid replacements within peptide sequences by reacting a zinc enolate intermediate with aldehydes. An efficient route has been developed to synthesize a proposed inhibitor for HCMV (Human Cytomegalovirus) protease by application of tandem chain extension-aldol reactions as the key step.
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New Reactions, Methodology, Heterocycles, Aromatics
8:00 PM-10:00 PM, Wednesday, August 25, 2004 Pennsylvania Convention Center -- Hall D, Poster
Division of Organic Chemistry |