Christopher D. VanderwalAssistant Professor, Chemistry |
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Research Interests |
natural product synthesis | |
| URL | Vanderwal Group Web Site | |
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Academic Distinctions |
Amgen Young Investigator Award, 2009 NSF CAREER Award, 2009 Thieme Synlett/Synthesis Journal Award, 2006 Lilly New Faculty Award, 2006 Amgen New Faculty Award, 2005 Bristol-Myers Squibb Graduate Fellowship in Synthetic Organic Chemistry, 2002 Roche Award for Excellence in Organic Chemistry, 2001 National Sciences and Engineering Research Council of Canada Graduate Scholarship, 1999-2001 |
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| Appointments | Jane Coffin Childs Memorial Fund for Medical Research Fellowship, Postdoctoral Fellow, Harvard University, 2003 to 2005 | |
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Research Abstract |
Our research program focuses on the development of strategies and methods for the rapid synthesis of architecturally complex natural products. Both target-inspired and methodology-driven approaches to synthesis are considered. | |
| Publications | Bedke, D. K.; Shibuya, G. M.; Pereira, A.; Gerwick, W. H.; Haines, T. H.; Vanderwal, C. D. Relative Stereochemistry Determination and Synthesis of the Major Chlorosulfolipid from Ochromonas danica Journal of the American Chemical Society, 2009, 131, 7570-7572. | |
| Steinhardt, S. E.; Vanderwal, C. D. Complex Polycyclic Lactams from Pericyclic Cascade Reactions of Zincke Aldehydes Journal of the American Chemical Society, 2009, 131, 7546-7547. | ||
| Martin, D. B. C.; Vanderwal, C. D. Efficient Access to the Core of the Strychnos, Aspidosperma and Iboga Alkaloids. A Short Synthesis of Norfluorocurarine. Journal of the American Chemical Society 2009, 131, 3472-3473. | ||
| Kanady, J. S.; Nguyen, J. D.; Ziller, J. W.; Vanderwal, C. D. Synthesis of All Four Diastereomers of 3,4-Dichloro-2-pentanol, Motifs Relevant to the Chlorosulfolipids Journal of Organic Chemistry 2009, 74, 21752178. | ||
| Bedke, D. K.; Vanderwal, C. D. Chlorine Lends a Helping Hand News and Views Article in Nature, 2009, 457, 548549. | ||
| Michels, T. D.; Rhee, J. U.; Vanderwal, C. D. Synthesis of d-Tributylstannyl-a,b,g,d-unsaturated Aldehydes from Pyridines Organic Letters 2008, 10, 47874790. | ||
| Shibuya, G. M.; Kanady, J. S.; Vanderwal, C. D. Stereoselective Dichlorination of Allylic Alcohol Derivatives to Access Key Stereochemical Arrays of the Chlorosulfolipids Journal of the American Chemical Society 2008, 130, 1251412518. | ||
| Steinhardt, S, E.; Silverston, J. S.; Vanderwal, C. D. "Stereocontrolled Synthesis of Z-Dienes via an Unexpected Pericyclic Cascade Rearrangement of 5-Amino-2,4-pentadienals" Journal of the American Chemical Society, 2008, 130, 7560-7561. | ||
| Bai, R.; Vanderwal, C. D.; Diaz, J. F.; Hamel, E. "Interaction of a Cyclostreptin Analogue with the Microtubule Taxoid Site: The Covalent Reaction Rapidly Follows Binding" Journal of Natural Products, 2008, 71, 370374. | ||
| Buey, R. M.; Calvo, E.; Barasoain, I.; Pineda, O.; Edler, M. C.; Matesanz, R.; Cerezo, G.; Vanderwal, C. D.; Day, B. W.; Sorensen, E. J.; Lopez, J. A.; Andreu, J. M.; Hamel, E. H.; Diaz, J. F. "Cyclostreptin Binds Covalently to Microtubule Pores and Lumenal Taxoid Binding Sites" Nature Chemical Biology, 2007, 3, 117-125. | ||
| Kearney, A. M.; Vanderwal, C. D. "Synthesis of Nitrogen Heterocycles by the Ring Opening of Pyridinium Salts" Angewandte Chemie International Edition, 2006, 45, 7803-7806. | ||
| Edler, M. C.; Buey, R. M.; Gussio, R.; Marcus, A. I.; Vanderwal, C. D.; Sorensen, E. J.; Diaz, J. F.; Giannakakou, P.; Hamel, E. "Cyclostreptin (FR182877), an Antitumor Tubulin-Polymerizing Agent Deficient in Enhancing Tubulin Assembly Despite Its High Affinity for the Taxoid Site" Biochemistry, 2005, 44, 11525-11538. | ||
| Vanderwal, C. D.; Jacobsen, E. N. "Enantioselective Formal Hydration of a,b-Unsaturated Imides by Al-Catalyzed Conjugate Addition of Oxime Nucleophiles" Journal of the American Chemical Society, 2004, 126, 14724-14725. | ||
| Vanderwal, C. D.; Sorensen, E. J. "A Remarkable Architectural Self- Construction Process is Discovered in a Synthesis of FR182877" In Strategies and Tactics in Organic Synthesis; Harmata, M. Ed.; Elsevier Academic Press: Oxford, 2004; Vol. 5, pp 1-50. | ||
| Adam, G. C.; Vanderwal, C. D.; Sorensen, E. J.; Cravatt, B. F. "()-FR182877 is a Potent and Selective Inhibitor of Carboxylesterase-1" Angewandte Chemie International Edition, 2003, 42, 5480-5484. | ||
| Vanderwal, C. D.; Vosburg, D. A.; Weiler, S.; Sorensen, E. J. "An Enantioselective Synthesis of FR182877 Provides a Chemical Rationalization of Its Structure and Affords Multi-gram Quantities of Its Direct Precursor" Journal of the American Chemical Society, 2003, 125, 5393-5407. | ||
| Vosburg, D. A.; Vanderwal, C. D.; Sorensen, E. J. "A Synthesis of (+)-FR182877 Featuring Tandem Transannular Diels-Alder Reactions Inspired by a Postulated Biogenesis" Journal of the American Chemical Society, 2002, 124, 4552-4553. | ||
| Vanderwal, C. D.; Vosburg, D. A.; Sorensen, E. J. "Intramolecular Allenolate Acylations in Studies toward a Synthesis of FR182877" Organic Letters, 2001, 3, 4307-4310. | ||
| Vanderwal, C. D.; Vosburg, D. A.; Weiler, S.; Sorensen, E. J. "Postulated Biogenesis of WS9885B and Progress toward an Enantioselective Synthesis" Organic Letters, 1999, 1, 645-648. | ||
| Link to this profile | http://www.faculty.uci.edu/profile.cfm?faculty_id=5265 | |
| Last updated | 06/09/2009 | |
