Jimmy Wu

Associate Professor of Chemistry

Research in the Wu group focuses on the development of new reactions for  synthesizing compounds that have potential therapeutic value.  These include (4+3) and (3+2) cycloadditions with indole, redox chain reactions, etc.  In particular, we have identified molecules that can up-regulate the secretion of GLP-1 (glucagon-like peptide-1), inhibit the growth of MRSA, and induce apoptosis in leukemia cells.  For each of these projects, we have teamed up with biological collaborators to study mechanisms of action and identify more potent analogues.

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We are also interested in developing novel methods for constructing carbon-sulfur bonds.  Although sulfur-containing molecules are prominent in numerous areas of research, comparatively little effort has been devoted to their synthesis. Many well-known bioactive compounds, such as the β-lactam antibiotics (i.e. penicillins, cephalosporins, thienamycin), anti-inflammatory agents (i.e. Vioxx and Celebrex), H2-receptor antagonists (i.e. Tagamet, Zantac, Pepcid), biotin, lipoic acid, and glutathione contain sulfur. In fact, it has been demonstrated in several instances that replacing a carbon or oxygen atom with sulfur greatly enhances the bioactivity of certain compounds with respect to their oxygenated or carbon counterparts.

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6128 Burke Laboratories, Hanover NH 03755
HB 6128
Department:
Chemistry
Education:
A.B. Princeton University 1994-1998
Ph.D. Harvard University 2001-2005
Associate Chemist Merck Process Research 1999-2001

Selected Publications

“Dearomative Indole (3+2) Cycloaddition Reactions” Li, H.; Hughes, R. P.; Wu, J. J. Am. Chem. Soc. 2014136, 62886296

"Markovnikov-Selective Hydrothiolation of Styrenes: Application to the Synthesis of Stereodefined Trisubstituted Olefins" Savolainen, M. A.; Wu, J. Org. Lett. 201315, 38023804.

"Redox Chain Reaction - Indole and Pyrrole Alkylation with Unactivated Secondary Alcohols" Han, X.; Wu, J. Angew. Chem. Int. Ed. 2013, 52, 4637−4640.

"Ga(III)-Catalyzed Three-Component (4+3) Cycloaddition Reactions" Han, X.; Li, H.; Hughes, R. P.; Wu, J. Angew. Chem. Int. Ed. 2012, 51, 10390−10393.

"Palladium-Catalyzed Allylic Fluorination of Cinnamyl Phosphorothioate Esters" Lauer, A. M.; Wu, J. Org. Lett. 2012, 14, 5138−5141.

"Phosphorothioic Acids as Surrogates for H2S - Synthesis of Chiral Tetrahydrothiophenes" Robertson, F. J.; Wu, J. J. Am. Chem. Soc. 2012, 134, 2775−2780.

"Cu(I)-Catalyzed, alpha-Selective, Allylic Alkylation Reactions between Phosphorothioate Esters and Organomagnesium Reagents" Lauer, A. M.; Mahmud, F.; Wu, J. J. Am. Chem. Soc. 2011, 133, 9119−9112. (This report was highlighted in Synfacts 2011, 9, 1009.)

"Direct Annulation and Alkylation of Indoles with 2-Aminobenzyl Alcohols Catalyzed by TFA” Robertson, F. J.; Kenimer, B. D.; Wu, J. Tetrahedron 2011, 67, 4327−4332. (Invited Contribution - Symposium in Print: Tetrahedron Young Investigators Award for Prof. Dean Toste)

"Ga(OTf)3-Catalyzed Direct Substitution of Alcohols with Sulfur Nucleophiles” Han, X.; Wu, J. Org. Lett. 2010, 12, 5780−5782.

"Convenient Synthesis of Allylic Thioethers from Phosphorothioate Esters and Alcohols” Robertson, F. J.; Wu, J. Org. Lett. 2010, 12, 2668−2671.

"Mild Two-Step Process for the Transition-Metal-Free Synthesis of Carbon−Carbon Bonds from Allylic Alcohols/Ethers and Grignard Reagents” Han, X.; Zhang, Y.; Wu, J. J. Am. Chem. Soc. 2010, 132, 4104−4106. (This report was highlighted in Synfacts 2010, 6, 700.)

"Review of Recent Advances in Nucleophilic C-F Bond-forming Reactions" Wu, J. Tetrahedron Lett. 201455, 4289–4294

"Diethylphosphorothioic Acid" Wu, J. Encyclopedia of Reagents for Organic Synthesis2014, DOI: 10.1002/047084289X.rn01667

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