ORGN 582 |
| Nature provides a diverse array of structurally and mechanistically interesting secondary metabolites of biomedical relevance. The study of the fundamental chemical reactivity of these substances has provided a wealth of new chemical as well as biochemical insights. Our laboratory has developed a range of synthetic methodologies and strategies for utilization in tackling the total synthesis of several naturally occurring nitrogenous substances of both biomedical significance and biological intrigue. The underlying theme is a hypothesis-driven synthesis program where total synthesis technologies are utilized to penetrate biomechanistic and biosynthetic puzzles. We have been particularly interested in the biosynthesis of prenylated indole alkaloids, such as the paraherquamides, notoamides and stephacidins which share a common bicyclo[2.2.2]diazaoctane core. It is believed that this ring system arises biosynthetically, via an intramolecular Diels-Alder type of cycloaddition of an unactivated isoprene-derived vinyl group with an azadiene species generated from the cyclo-didpeptide progenitors. We have successfully completed biomimetic total syntheses of brevianamide B, VM55599, pre-paraherquamide, stephacidin A and notoamide B. Recent work in this area will be presented. |
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Biomimetic Natural and Unnatural Products Synthesis
1:00 PM-5:00 PM, Wednesday, March 28, 2007 McCormick Place Lakeside -- Room E451A/B, Level 4, Oral
Division of Organic Chemistry |