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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S. A. Snyder, N. E. Wright, J. J. Pflueger, S. P. Breazzano. Total Syntheses of Heimiol A, Hopeahainol D, and Constrained Analogs. Angew. Chem. Int. Ed., 2011, in press.
S. A. Snyder, A. Gollner, M. I. Chiriac. Regioselective Reactions for Programmable Resveratrol Oligomer Synthesis. Nature, 2011, 474, 461-466.
S. A. Snyder, D. A. Wespe, J. M. von Hof. A Concise, Stereocontrolled Total Synthesis of Rippertenol. J. Am. Chem. Soc., 2011, 133, 8850-8853. One of the top 5 Most Accessed Articles for May 2011
S. A. Snyder, F. Kontes, A. M. ElSohly. Mechanistic Investigations of the Cyclocondensation Step of the Knorr Pyrrole Synthesis. Heterocycles, 2011, 84, ASAP.Invited submission in honor of Prof. Albert Padwa's 75th Birthday
S. A. Snyder, F. Kontes. Explorations into Helicterin, Helisorin, and Helisterculin Biosynthesis via Diels-Alder Processes. Isr. J. Chem., 2011, 51, 378-390.
S. A. Snyder, D. S. Treitler, A. Schall. A Two-Step Mimic for Direct, Asymmetric Bromonium- and Chloronium-induced Polyene Cyclizations. Tetrahedron 2010, 66, 4796-4804. Invited submission in honor of Prof. Brian M. Stoltz' TYIA Award
S. A. Snyder, S. P. Breazzano, A. G. Ross, Y. Lin, A. L. Zografos, "Total Synthesis of Diverse Carbogenic Complexity within the Resveratrol Class from a Common Building Block," J. Am. Chem. Soc. 131, 1753-1765 (2009)
S. A. Snyder, F. Kontes, "Explorations into Neolignan Biosynthesis: Total Synthesis of Helicterin B, Helisorin, and Helisterculin A from a Common Intermediate," J. Am. Chem. Soc. 131, 1745-1752 (2009)
S. A. Snyder, A. L. Zografos, Y. Lin, "Total Synthesis of Resveratrol-based Natural Products: A Chemoselective Approach," Angew. Chem. 119, 8334-8339 (2007); Angew. Chem. Int. Ed. 2007, 46, 8186-8191 (2007)
S. A. Snyder, E. J. Corey, "Concise Total Syntheses of Palominol, Dolabellatrienone, β-Araneosene, and Isoedunol Via an Enantioselective Diels-Alder Macrobicyclization," J. Am. Chem. Soc. 128, 740-742 (2006)
S. A. Snyder, E. J. Corey, "Regioselective Aldol Condensations of a Cholestanone-Derived Dialdehyde: New Twists on a Classic Reaction," Tetrahedron Lett. 47, 2083-2086 (2006)
K. C. Nicolaou, S. A. Snyder, D. A. Longbottom, A. Z. Nalbandian, X. Huang. New Uses for the Burgess Reagent in Chemical Synthesis: Methods for the Facile and Stereoselective Formation of Sulfamidates, Glycosylamines, and Sulfamides, Chem. Eur. J. 10, 5581-5606 (2004)
K. C. Nicolaou, J. Hao, M. V. Reddy, P. Bheema Rao, G. Rassias, S. A. Snyder, X. Huang, D. Y.-K. Chen, W. E. Brenzovich, N. Giuseppone, A. O'Brate, P. Giannakakou, "Chemistry and Biology of Diazonamide A: Second Total Synthesis and Biological Investigations" J. Am. Chem. Soc. 126, 12897-12906 (2004)
K. C. Nicolaou, D. Y.-K. Chen, X. Huang, T. Ling, M. Bella, S. A. Snyder, "Chemistry and Biology of Diazonamide A: First Total Synthesis and Confirmation of the True Structure" J. Am. Chem. Soc. 126, 12888-12896 (2004)
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, "Studies Toward Diazonamide A: Development of Hetero Pinacol Macrocyclization Cascade for the Construction of the Bis-Macrocyclic Framework of the Originally Proposed Structure" J. Am. Chem. Soc. 126, 10174-10182 (2004)
K. C. Nicolaou, S. A. Snyder, A. Z. Nalbandian, D. A. Longbottom, "A New Method for the Stereoselective Synthesis of α- and β-Disposed Glycosylamines Using the Burgess Reagent" J. Am. Chem. Soc. 126, 6234-6235 (2004)
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