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Research Summary
Throughout the course of its history, the total synthesis of natural products has served as a principal driving force for discovering new chemical reactivity, evaluating physical organic theories, testing the power of existing synthetic methods, and enabling biology and medicine. Indeed, retrosynthetic analysis, carbodiimide-based peptide coupling reagents, cation-pi cyclizations, frontier molecular orbital theory, chiral auxiliaries, catalysts for asymmetric reactions, silyl protecting groups, and several designed pharmaceuticals are but a few of the landmark achievements that have derived from its inspirational power. Hundreds of equally important discoveries undoubtedly remain, and our research program seeks to unearth some of these treasures.
Our mines are some of the most complex families of natural products currently known in the literature. Utilizing their unique architectures as catalysts for innovation, our group seeks to accomplish their efficient construction through the design and development of new strategies, biomimetic tactics, cascade sequences, and synthetic methods that will hopefully provide general solutions applicable to hosts of other molecules. In addition, by having selected ornate targets, chances are high that additional synthetic wealth will result from intermediates following non-prescribed pathways in the designed sequence, thereby opening windows into new modes of chemical reactivity that can be tapped to solve other problems.
Once the target molecules have been completed, additional explorations into their chemical biology will be made when appropriate. Such investigations might include the design and synthesis of analogs bearing deep-seated structural modifications as well as the identification of their specific biological targets and/or mechanism of action.
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“Concise Total Syntheses of Palominol, Dolabellatrienone, b--Araneosene, and Isoedunol Via an Enantioselective Diels–Alder Macrobicyclization,” S. A. Snyder, E. J. Corey, J. Am. Chem. Soc. 128, 740-742 (2006).
“Chasing Molecules That Were Never There: Misassigned Natural Products and the Role of Chemical Synthesis in Modern Structure Elucidation,” K. C. Nicolaou, S. A. Snyder, Angew. Chem. Int. Ed. 44, 1012-1044 (2005).
“Studies Towards Diazonamide A: Initial Synthetic Forays Towards the Originally Proposed Structure,” K. C. Nicolaou, S. A. Snyder, X. Huang, K. B. Simonsen, A. E. Koumbis, A. Bigot, J. Am. Chem. Soc. 126, 10162-10173 (2004).
“Studies Towards Diazonamide A: Development of Hetero Pinacol Macrocyclization Cascade for the Construction of the Bis-Macrocyclic Framework of the Originally Proposed Structure,” K. C. Nicolaou, S. A. Snyder, N. Giuseppone, X. Huang, M. Bella, M. V. Reddy, P. Bheema Rao, A. E. Koumbis, A. O’Brate, P. Giannakakou, J. Am. Chem. Soc. 126, 10174-10182 (2004).
“A New Method for the Stereoselective Synthesis of a- and b-Disposed Glycosylamines Using the Burgess Reagent,” K. C. Nicolaou, S. A. Snyder, A. Z. Nalbandian, D. A. Longbottom. J. Am. Chem. Soc. 126, 6234-6235 (2004).
“Classics in Total Synthesis II: More Targets, Strategies, Methods,” K. C. Nicolaou, S. A. Snyder, Wiley-VCH, Weinheim, p. 639 (2003).
“The Diels–Alder Reaction in Total Synthesis.” K. C. Nicolaou, S. A. Snyder, T. Montagnon, G. E. Vassilikogiannakis, Angew. Chem. Int. Ed. 41, 1668-1698 (2002).
“Solution and Solid Phase Synthesis of Functionalized 3-Arylbenzofurans via a Novel Cyclofragmentation Pathway,” K. C. Nicolaou, S. A. Snyder, A. Bigot, J. A. Pfefferkorn, Angew. Chem. Int. Ed. 39, 1036-1039 (2000).
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