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.
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.
“Dearomative Indole (3+2) Reactions with Azaoxyallyl Cations − New Method for the Synthesis of Pyrroloindolines” DiPoto, M. C.; Hughes, R. P.; Wu, J. J. Am. Chem. Soc. 2015, 137, ASAP.
“Vinylogous Mukaiyama−Michael Reactions of Dihydropyridinones” Li, H.; Wu, J. Org. Lett. 2015, 17, 5424−5427.
“Total Syntheses and Biological Evaluation of Both Enantiomers of Several Hydroxylated Dimeric Nuphar Alkaloids” Korotkov, A.; Li, H.; Chapman, C. W.; Xue, H.; MacMillan, J. B.; Eastman, A.; Wu, J. Angew. Chem. Int. Ed. 2015, 54, 10604-10607.
"Regioselective Formal Hydroamination of Styrenes with 1-Phenyl-1H-tetrazole-5-thiol" Savolainen, M. A.; Han, X.; Wu, J. Org. Lett. 2014, 16, 4349−4351.
"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.
"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.)
"(3+2)-Cycloaddition Reactions of Oxyallyl Cations” Li, H.; Wu, J. Synthesis 2015, 47, 22−33.
"Diethylphosphorothioic Acid" Wu, J. Encyclopedia of Reagents for Organic Synthesis, 2014, DOI: 10.1002/047084289X.rn01667