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Christopher D. Vanderwal

Associate Professor and Chancellor's Fellow, Chemistry
School of Physical Sciences

Ph.D., The Scripps Research Institute, 2003, Chemistry

Phone: (949)-824-6702
Fax: (949)-824-2210
Email: cdv@uci.edu

University of California, Irvine
1102 Natural Sciences II
Department of Chemistry
Mail Code: 2025
Irvine, CA 92697

picture of Christopher D. Vanderwal

Research
Interests
natural product synthesis
   
URL Vanderwal Group Web Site
   
Academic
Distinctions
UCI Chancellor's Fellow, 2011-2013
Eli Lilly Grantee, 2010
AstraZeneca Award for Excellence in Chemistry, 2010
Fellow of the A. P. Sloan Foundation, 2010
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
   
Appointments Jane Coffin Childs Memorial Fund for Medical Research Fellowship, Postdoctoral Fellow, Harvard University, 2003 to 2005
   
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 Vanderwal, C. D. “Reactivity and Synthesis Inspired by the Zincke Ring-Opening of Pyridines” Perspective Article in Journal of Organic Chemistry doi: 10.1021/jo201625e, published online 30 August 2011.
   
  Martin, D. B. C.; Vanderwal, C. D. “A Synthesis of Strychnine via a Longest Linear Sequence of Six Steps” Chemical Science 2011, 2, 649–651.
   
  Bedke, D. K.; Vanderwal, C. D. “Chlorosulfolipids: Structure, Synthesis, and Biological Relevance” Natural Product Reports 2011, 28, 15–25.
   
  Paton, R. S.; Steinhardt, S. E.; Vanderwal, C. D.; Houk, K. N. "Unraveling the Mechanism of Cascade Reactions of Zincke Aldehydes" Journal of the American Chemical Society 2011, 133, 3895-3905.
   
  Dowling, M. S.; Vanderwal, C. D. “Ring-Closing Metathesis of Allylsilanes as a Flexible Strategy Toward Cyclic Terpenes. Short Syntheses of Teucladiol, Isoteucladiol, Poitediol and Dactylol, and an Attempted Synthesis of Caryophyllene” Journal of Organic Chemistry 2010, 75, 6908–6922.
   
  Michels, T. D.; Kier, M. J.; Kearney, A. M.; Vanderwal, C. D. "Concise Formal Syntheses of Porothramycins A and B via Zincke Pyridinium Ring-Opening/Ring-Closing Cascade" Organic Letters, 2010, 13, 3093–3095.
   
  Bedke, D. K.; Shibuya, G. M.; Pereira, A. R.; Gerwick, W. H.; Vanderwal, C. D. “A Concise Enantioselective Synthesis of the Chlorosulfolipid Malhamensilipin A” Journal of the American Chemical Society 2010, 132, 2542-2543.
   
  Pereira, A. R.; Byrum, T.; Shibuya, G. M.; Vanderwal, C. D.; Gerwick, W. H. “Structure Revision and Absolute Configuration of Malhamensilipin A from the Freshwater Chrysophyte Poterioochromonas malhamensis.” Journal of Natural Products 2010, 73, 279-283.
   
  Dowling, M. S.; Vanderwal, C. D. “Ring-Closing Metathesis of Allylsilanes/Electrophilic Desilylation to Prepare exo-Methylidenecycloalkanes. Short Syntheses of Teucladiol and Poitediol” Journal of the American Chemical Society 2009, 131, 15090–15091.
   
  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, 2175–2178.
   
  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, 4787–4790.
   
  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, 12514–12518.
   
  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.
   
  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.
   
Grants NSF CAREER Grant, 2009–2014
   
NIH R01 grant from NIGMS, 2010–2014
   
   
Link to this profile http://www.faculty.uci.edu/profile.cfm?faculty_id=5265
   
Last updated 11/09/2011