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Peter Wipf

Peter Wipf
University Professor
Total Synthesis of Natural Products; Organometallic and Heterocyclic Chemistry; Combinatorial Synthesis

Department of Chemistry
Chevron Science Center
219 Parkman Avenue
Pittsburgh, PA 15260
Office: 1301 CHVRN
Telephone: 412-624-8606
Fax: 412-624-0787
E-Mail: pwipf@pitt.edu
Website

Total Synthesis of Natural Products Total Synthesis encompasses all aspects of organic chemistry: The development of new methodology, mechanistic and physical organic experiments, conformational and configurational analysis by spectroscopic and computational methods, and bioorganic and medicinal chemistry. Total Synthesis is also one of the broadest and most rewarding educational experiences for aspiring synthetic chemists.

Organometallic Chemistry Organometallic Chemistry will provide most of new revolutionary techniques for C,C and C-heteroatom bond formations and asymmetric catalysis. Our group has had a long tradition in synthetic applications of transition metals.

Heterocyclic Chemistry More than half of all known organic compounds, and the vast majority of drugs, are heterocyclic. We are interested in the development of new stereoselective methods for the preparation of highly functionalized heterocycles. In particular, we have developed novel protocols for five-membered heterocycle synthesis that have been widely adopted in industry and academe.

Combinatorial Synthesis We apply combinatorial chemistry and solid phase synthesis methods for reagent and catalyst design in organometallic and heterocyclic chemistry, and for the structure-activity analysis of bioactive natural products. Specifically, we are involved in collaborative drug development for cancer therapy. Some of these projects take advantage of the infrastructure of the Combinatorial Chemistry Center (CCC).

Computational Prediction of Macroscopic Properties In another exciting interdisciplinary collaboration, we have joined forces with the Beratan group for the computational assignment of the relative and absolute stereochemistry of organic molecules of organic molecules and the theoretical prediction of chiroptical phenomena.

Awards

• Fellow of the Royal Society of Chemistry (FRSC, 2004) • Visiting Professor (Professeur Associé), École Supérieur de Physique et de Chimie Industrielles de la Ville de Paris (ESPCI), Paris, France (September 2004) • Long Range Planning Committee, ACS Division of Medicinal Chemistry (2004-2006) • ISHC Katritzky Award in Heterocyclic Chemistry (2003) • Fellow of the American Association for the Advancement of Science (AAAS, 2002) • Chair, Gordon Research Conference on Stereochemistry, Salve Regina University, Newport, Rhode Island (June 9-14, 2002) • Visiting Professor (Professeur Associé), Université de Paris-Sud, Orsay, France (November 2001) • Member-at-Large, Organic Division Executive Committee of the ACS (2001-2003) • Chair of the Organic Division, University of Pittsburgh (2001-2004) • Novartis Research Award (2000, 2001) • Japan Society for the Promotion of Science Fellow (2000) • Akron Section ACS Award (1998) • Arthur C. Cope Scholar Award (1998) • NIH Medicinal Chemistry Study Section, Member, 1998-2003, Chairman, 2001-2003 • Chancellor’s Distinguished Research Award (1997) • Phi Eta Sigma, Honorary Member (1996) • Merck Young Investigator Award (1995) • Zeneca Award for Excellence in Chemistry (1995) • Camille Dreyfus Teacher-Scholar Award (1995) • UCI-Allergan Visiting Lecturer, University of California, Irvine, California (May, 1995) • American Cancer Society Junior Faculty Research Award (1995-1998) • NSF Presidential Faculty Fellow (1994-1999) • ETH Ruzicka Award (1994) • Alfred P. Sloan Research Fellow (1994-1996) • American Cyanamid Faculty Award (1994) • Eli Lilly Grantee (1993-1995) • University of Zürich, Distinguished Dissertation Award (1987).

Selected Publications

"New Antiestrogens from a Library Screen of Homoallylic Amines, Allylic Amines, and C-Cyclopropylalkylamines.," Janjic, J. M.; Mu, Y.; Kendall, C.; Stephenson, C. R. J.; Balachandran, R.; Raccor, B. S.; Lu, Y.; Zhu, G.; Xie, W.; Wipf, P.; Day, B. W., Bioorg. Med. Chem., 2005, 13, 157-164

"Asymmetric Total Syntheses of Tuberostemonine, Didehydrotuberostemonine and 13-Epituberostemonine.," Wipf, P.; Rector, S. R., J. Am. Chem. Soc., 2005, 127, 225-235

"Convergent Approach to (E)-Alkene and Cyclopropane Peptide Isosteres.," Wipf, P.; Xiao,J., Org. Lett., 2005, 7, 103-106

"Silver(I)-Catalyzed Addition of Zirconocenes to Glycal Epoxides. A New Synthesis of á-C-Glycosides.," Wipf, P.; Pierce, J. G.; Zhuang, N., Org. Lett., 2005, 7, 483-485

"Microwave-Assisted “Libraries from Libraries” Approach toward the Synthesis of Allyl- and C-Cyclopropylalkylamides.," Wipf, P.; Coleman, C. M.; Janjic, J. M.; Iyer, P. S.; Fodor, M. D.; Shafer, Y. A.; Stephenson, C. R. J.; Kendall, C.; Day, B. W., J. Comb. Chem., 2005, 7, 322-330

"Three-Component Synthesis of á,â-Cyclopropyl-ã-Amino Acids.," Wipf, P.; Stephenson, C. R. J., Org. Lett., 2005, 7, 1137-1140

"Electrostatic vs Steric Effects in Peptidomimicry. Synthesis and Secondary Structure Analysis of Gramicidin S Analogs with (E)-Alkene Peptide Isosteres.," Wipf, P.; Xiao, J., J. Am. Chem. Soc., 2005, 127, 5742-5743

"Diversity-Oriented Synthesis of Azaspirocycles.," Wipf, P.; Stephenson, C. R. J.; Walczak, M. A. A., Org. Lett., 2004, 6, 3009-3012

"Small Molecule Modulators of Endogenous and Co-Chaperone-Stimulated Hsp70 ATPase Activity.," Fewell, S. W.; Smith, C. M.; Lyon, M. A.; Dumitrescu, T. P.; Wipf, P.; Day, B. W.; Brodsky, J. L., J. Biol. Chem., 2004, 279, 51131-51140

"Total Synthesis of (-)-Disorazole C1.," Wipf, P.; Graham, T. H., J. Am. Chem. Soc., 2004, 126, 15346-15347