Joseph J. Topczewski

Assitant Professor of Chemistry

B.S. University of Wisconsin at Parkside, 2007

Ph.D. University of Iowa, 2011, David Wiemer

Post Doctorate University of Iowa, 2011-2013, Hien Nguyen and Daniel Quinn,

                             University of Michigan, 2013-2015, Melanie Sanford

E: jtopczew@umn.edu

T: (612) 624-8095

Office: 568B Kolthoff Hall

 

     Professor Topczewski (Joe) was born in southeastern Wisconsin and grew up in the city of Racine. He attended the University of Wisconsin at Parkside and graduated in 2007 after conducting research with Prof. Lori Allen. Joe moved to the University of Iowa for graduate school and graduated in 2011. Joe worked with Prof. David Wiemer and synthesized many schweinfurtin natural products and analogues as part of a collaboration with the National Cancer Institute. During this time, he explored the utility of a cascade cyclization terminated by an electrophilic aromatic substitution. Joe was awarded a predoctoral fellowship from the ACS Medicinal Chemistry Division for this work. After graduation, Joe stayed in Iowa City for two additional years. During this time, he worked with Prof. Hien Nguyen to develop an enantioselective iridium catalyzed (radio-)fluorination. Joe also worked with Prof. Dan Quinn to develop new antidotes for sarin agents by re-activating AChE. After his wife Anna completed her degree, Joe moved to the University of Michigan and joined the lab of Prof. Melanie Sanford.  While at Michigan, Joe collaborated with Prof. Peter Scott and Dr. Naoko Ichiishi on new methods of radio-fluorination. A second project was funded (NIH-F32) and Joe shifted his attention to the C-H activation of piperidine derivatives.

     In the summer of 2015, Joe moved to the Twin–Cities and started his independent career. At the University of Minnesota, Joe’s lab focuses on developing new and efficient methods of chemical synthesis. Joe is exceptionally passionate about developing highly selective reactions and on reactions that exploit dynamic systems. To this end, one major thrust of his lab's research involves the selective differentiation of allylic azides. Outside the lab, Joe and Anna love living in the Twin Cities. They enjoy gardening, walking our dogs, rooting for the Packers, visiting downtown, and playing the occasional board game. 

Independent Publications:

Publications

Mentored Publications:

23) Quinn, D. M.; Topczewski, J. J.; Yasapala, N.; Lodge, A. "Why is Aged Acetylcholinesterase So Difficult to Reactivate?" Molecules 2017, 22, 1464. ( DOI:10.3390/molecules22091464)

22) Topczewski, J. J.; Topczewski, A. M.; Tang, H.; Kendhammer, L. K.; Pienta, N. J. “NMR Spectra through the Eyes of a Student: Eye Tracking Applied to NMR Items” J. Chem. Ed. 2017, 94, 29. (DOI:10.1021/acs.jchemed.6b00528)

21) Topczewski, J. J.; Cabrera, P. J.; Saper, N. I.; Sanford, M. S. “Palladium-Catalyzed Transannular C–H Functionalization of Alicyclic Amines” Nature, 2016531, 220. (DOI:10.1038/nature16957)

20) Morril, J. A.; Topczewski, J. J.; Lodge, A. M.; Yasapala, N. Y.; Quinn, D. M. “Development of quantitative structure activity relationships for the binding affinity of methoxypyridinium cations for human acetylcholinesterase” J. Mol. Graphics Modell, 201562, 181. (DOI:10.1016/j.jmgm.2015.09.016)

19) Zhang, Q.; Stockdale, D.; Mixdorf, J. C.; Topczewski, J. J.; Nguyen, H. M. “Iridium-Catalyzed Enantioselective Fluorination of Racemic, Secondary Allylic Trichloroacetimidates” J. Am. Chem. Soc. 2015137, 11912. (DOI: 10.1021/jacs.5b07492).

18) Ichiishi, N.; Brooks, A. F.; Topczewski, J. J.; Rodnick, M. E.; Sanford, M. S.; Scott, P. J. H. “[18F]Fluorination of (Mesityl)(Aryl)Iodonium Salts” Radiochemical Syntheses, 2015, Ch.14. (DOI: 10.1002/9781118834114.ch14)

17) Topczewski, J. J.; Sanford, M. S. “Carbon-Hydrogen (C-H) Bond Activation at Pd(IV): A Frontier in Catalysis” Chem. Sci. 20156, 70. (Invited Review) (DOI: 10.1039/c4sc02591a)

16) Brooks, A. F.; Topczewski, J. J.; Ichiishi, N.; Sanford, M. S.; Scott, P. J. H. “Late-stage [18F]Fluorination: New Solutions to Old Problems” Chem. Sci. 20145, 4545. (DOI: 10.1039/C4SC02099E)

15) Ichiishi, N.; Brooks, A. F.; Topczewski, J. J.; Rodnick, M. E.; Sanford, M. S.; Scott, P. J. H. “Copper-Catalyzed [18F]Fluorination of (Mesityl)(aryl)iodonium Salts” Org. Lett. 201416, 3224. (DOI: 10.1021/ol501243g)

14) Scott, P. J. H.; Sanford, M. S.; Ichiishi, N.; Brooks, A. F.; Rodnick, M. E. and Topczewski, J. J. "Copper Catalyzed [18F]Fluorination of Iodonium Salts" U. S. Patent Application Serial Number 61/978,646, filed 11 April 2014.

13) Quinn, D. M. and Topczewski, J. J. "Compounds and Methods to Treat Organophosphorus Poisoning" U. S. Patent Application Number 14163859, filed 24 January 2014.

12) Topczewski, J. J.; Lodge, A. M.; Yasapala, S. N.; Payne, M. K.; Keshavarzi, P. M.; Quinn, D. M. “Reversible Inhibition of Human Acetylcholinesterase by Methoxypyridinium Species” Bioorg. Med. Chem. Lett. 201323, 5786. (DOI:10.1016/j.bmcl.2013.09.008)

11) Kodet, J. G.; Topczewski, J. J.; Gardner, K. D.; Wiemer, D. F. “Electrophilic Prenylation via Cascade Cyclization” Tetrahedron, 201344, 9212. (DOI: 10.1016/j.tet.2013.08.056)

10) Topczewski, J. J.; Quinn, D. M. “Kinetic Assessment of N-Methyl-2-Methoxypyridinium Species as Phosphonate Anion Methylating Agents” Org. Lett. 201315, 1084. (DOI: 10.1021/ol400054m)

9) Topczewski, J. J.; Tewson, T. J.; Nguyen, H. M. “Iridium-Catalyzed Allylic Fluorination of Trichloroacetimidates” J. Am. Chem. Soc. 2011133, 19318. (DOI: 10.1021/ja2087213)

8) Topczewski, J. J. “Cascade Cyclizations and the Schweinfurthins” Ph.D. Thesis, University of Iowa, Iowa City, IA, 2011. 

7) Topczewski, J. J.; Callahan, M. P.; Kodet, J. G.; Inbarasu, J. D.; Mente, N. R.; Beutler, J. A.; Wiemer, D. F. “Relevance of the C-5 Position to Schweinfurthin Induced Cytotoxicity” Bioorg. Med. Chem. 201119, 7570. (DOI: 10.1016/j.bmc.2011.10.034)

6) Topczewski, J. J.; Wiemer, D. F. “First Total Synthesis of (+)-Vedelianin, a Potent Anti-proliferative Agent” Tetrahedron Lett. 201152, 1628. (DOI:10.1016/j.tetlet.2011.01.137)

5) Topczewski, J. J.; Kodet, J. G.; Wiemer, D. F. “Exploration of Cascade Cyclizations Terminated by Tandem Aromatic Substitution: Total Synthesis of (+)-Schweinfurthin A” J. Org. Chem. 201176, 909. (DOI: 10.1021/jo1022102)

4) Topczewski, J. J.; Kuder, C. H.; Neighbors, J. D.; Hohl, R. J.; Wiemer, D. F. “Fluorescent Schweinfurthin B and F Analogs with Anti-proliferative Activity” Bioorg. Med. Chem. 201018, 6734. (DOI: 10.1016/j.bmc.2010.07.056)

3) Topczewski, J. J.; Callahan, M. P.; Neighbors, J. D.; Wiemer, D. F. “A Tandem Cascade Cyclization-Electrophilic Aromatic Substitution: Application in the Total Synthesis of (+)-Angelichalcone” J. Am. Chem. Soc. 2009131, 14630. (DOI: 10.1021/ja906468v)

2) Topczewski, J. J.; Neighbors, J. D.; Wiemer, D. F. “Total Synthesis of (+)-Schweinfurthins B and E” J. Org. Chem. 200974, 6965. (DOI: 10.1021/jo901161m)

1) Neighbors, J. D.; Topczewski, J. J.; Swenson, D. C.; Wiemer D. F. “Synthesis of the Cis-Fused Hexahydroxanthene System via Cationic Cascade Cyclization” Tetrahedron Lett. 200950, 3881. (doi:10.1016/j.tetlet.2009.04.052)

Joe