ORGN 485 |
| Dongmei Han, Xiaoxiang Liu, and James M. Cook. Department of Chemistry, University of Wisconsin-Milwaukee, 3210, N. Cramer Str, Milwaukee, WI 53211 |
| The Pictet-Spengler reaction is one of the most important reactions in indole alkaloid chemistry. Although kinetic studies performed under neutral conditions indicated little difference in cyclization rates between 6-methoxytryptophan derivatives and their unsubstituted counterparts, the epimerization rates measured in the presence of TFA, however, were significantly faster for the 6-substituted derivatives. These findings suggest that epimerization occurs via a carbocationic, ring-opening pathway. |
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Total Synthesis, Asymmetric Reactions and Syntheses, Bioorganic
9:00 AM-11:00 AM, Wednesday, March 31, 2004 Anaheim Convention Center -- Hall C, Poster
Division of Organic Chemistry |
