pavel

Pavel obtained his B.S. degree from Oregon State University in 2001 where he conducted his undergraduate research studies with Prof. James D. White. He earned his Ph.D. from Harvard University 2007), working on the total synthesis of oasomycin A in the laboratory of Prof. David A. Evans. He later moved to Memorial Sloan-Kettering Cancer Center where he conducted research with Prof. Samuel J. Danishefsky working on synthesis of homogeneous human Follicle-Stimulating Hormone (h-FSH), small cell lung cancer vaccines, and migrastatin-based antimetastatic agents (2007-2010). In 2010 Pavel joined the faculty of the University of Michigan Chemistry Department as an assistant professor of chemistry, and in 2017 was promoted to the rank of associate professor with tenure, and in 2022 to the rank of full professor. His current research interests are in the areas of organocatalysis, natural product synthesis, carbohydrate chemistry and medicinal chemistry.

Education and Training:

 

2022 – Current Professor of Chemistry, Affiliated Faculty, Medicinal Chemistry and Program in Chemical Biology, University of Michigan Ann Arbor, MI                                  

2017   2022   Associate Professor of Chemistry, Affiliated Faculty, Medicinal Chemistry, University of Michigan, Ann Arbor, MI

2014 – 2017 William R. Roush Assistant Professor of Chemistry, Affiliated Faculty, Medicinal Chemistry, University of Michigan, Ann Arbor, MI

2010 – 2013 Robert A. Gregg Assistant Professor of Chemistry, Affiliated Faculty, Medicinal Chemistry, University of Michigan, Ann Arbor, MI
2007 – 2010 Postdoctoral Fellow, Memorial Sloan–Kettering Cancer Center, New York, NY
2001 – 2007 Ph.D. in Chemistry; Dissertation Title: Total Synthesis of Oasomycin A, Harvard University, Cambridge, MA
1998 – 2001 B.S. in Chemistry, Oregon State University, Corvallis, OR

Awards and Honors:

 

2015 Amgen Young Investigators' Award

2014 Sloan Foundation Fellowship

2014 NSF Career Award

2012 Thieme Chemistry Journal Award

 

Prior to the University of Michigan:
2007 – 2010 NIH, Ruth L. Kirschstein Postdoctoral Fellowship
2004 – 2005 Eli Lilly Organic Chemistry Fellowship (Harvard University)
2003 – 2004 Christensen Travel Grant (Harvard University)
2000 – 2001 Merck Index Award (Oregon State University)
1999 – 2000 Dean's Scholarship in the Natural Sciences (Oregon State University)
1999 – 2000 ACS Award in Analytical Chemistry (Oregon State University)

Peer-Reviewed Publications as Assistant Professor (University of Michigan):

 

Please see the "Publications" section for the full list. 

46)  Kim, S.; Khomutnyk, Y.; Bannykh, A.; Nagorny, P. "Synthesis of glycosyl fluorides by photochemical fluorination with sulfur(VI) hexafluoride" Org. Lett. 2020, In Press.

45) Diaz, N.; Nagorny, P. "(11bR)-4-Hydroxy-2,6-bis[2,4,6-tris(1-methylethyl)phenyl]-dinaphtho[2,1-d: 1',2'-f][1,3,2]dioxaphosphepin-4-oxide, [(R)-TRIP] & (11bS)-4-Hydroxy-2,6-bis[2,4,6-tris(1-methylethyl)phenyl]-dinaphtho[2,1-d: 1',2'-f][1,3,2]dioxaphosphepin-4-oxide, [(S)-TRIP]" (Update) Encyclopedia of Reagents in Organic Synthesis 2020, In Production.

44) Sun, S.; Nagorny, P. "Exploration of chiral diastereomeric spiroketal (SPIROL)-based phosphinite ligands in asymmetric hydrogenation of heterocycles" Chem. Commun. 2020, 56, 8432.

43) Wang, S.; Arguelles, A. J.; Tay, J.-H.; Hotta, M.; Zimmerman, P. M.*; Nagorny, P.* "Experimental and computational studies on regiodivergent chiral phosphoric acid catalyzed cycloisomerization of mupirocin methyl ester" Chem. Eur. J. 2020, 26, 4583 (hot article).

42) Khatri, H. R.; Carney, N.; Rutkoski, R.; Bhattarai, B.; Nagorny, P. "Recent progress in steroid synthesis triggered by the emergence of new catalytic methods" Eur. J. Org. Chem. 2020, 21, 755 (Invited Minireview).

41) Khatri, H. R.; Bhattarai, B.; Kaplan, W.; Li, Z.; Long, M. J. C.*; Aye, Y.*; Nagorny, P.* “Modular Total Synthesis and Cell-based Anticancer Activity Evaluation of Ouabagenin and Other Cardiotonic Steroids with Varying Degrees of Oxygenation” J. Am. Chem. Soc. 2019, 141, 4849.

40) Tay, J.-H.; Dorokhov, V.; Wang, S.; Nagorny, P.* “Regioselective Single Pot C3-Glycosylation of Strophanthidol Using Methylboronic Acid as a Traceless Protecting Group” (Invited Contribution for the Special Issue Dedicated to Professor Samuel Danishefsky) J. Antibiotics 2019, 72, 437.

39) Kearney, S. E. et al. “Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space” ACS Cent. Sci. 2018, 4, 1727.

38) Lee, J.; Wang, S.; Callahan, M.; Nagorny, P.* "Copper(II)-catalyzed tandem decarboxylative Michael/Aldol reactions leading to the formation of functionalized cyclohexenones" Org. Lett., 2018, 20, 2067.

37) Arguelles, A. J.; Sun, S.; Budaitis, B.; Nagorny, P.* "Design, synthesis and application of novel chiral C2-symmetric spiroketal-containing ligands in transition metal catalysis" Angew. Chem. Int. Ed., 2018, 57, 5325.

36) Bhattarai, B.; Nagorny, P.* "Enantioselective total synthesis of cannogenol-3-O-a-L-rhamnoside via sequential Cu(II)-catalyzed Michael addition/intramolecular aldol cyclization reactions" Org.Lett., 2018, 20, 154.

35) Lee, J.; Borovika, A.; Khomutnyk, Y.; Nagorny, P.* "Chiral phosphoric acid-catalyzed desymmetrizative glycosylation of 2-deoxystreptamine and its application to aminoglycoside synthesis" Chem. Commun., 2017, 53, 8976. (themed issue "Site Selective Molecular Transformations").

34) Tay, J.-H.; Nagorny, P.* "Bronsted Acid Catalysts Derived from Phosphorous" Non-nitregenous Organocatalysis, Chapter 3, 2017 (edited by Andrew Harned), In Production.

33) Tay, J.-H.; Arguelles, A. J.; DeMars II, M. D.; Zimmerman, P. M.;* Sherman, D. H.;* Nagorny, P.* "Regiodivergent Glycosylations of 6-deoxy-Erythronolide B and Oleandomycin-derivied Macrolides Enabled by Chiral Acid Catalysis" J. Am. Chem. Soc. 2017, In Press.

32) Nagorny, P., Sun, Z. "New Approaches to Organocatalysis Based on C–H and C–X bonding for Electrophilic Substrate Activation" Beilstein Journal of Chemistry 2016,12, 2834.

31) Kaplan, W.; Khatri, H. R.; Nagorny, P. "Concise Enantioselective Total Synthesis of Cardiotonic Steroids 19-Hydroxysarmentogenin and Trewianin Aglycone" J. Am. Chem. Soc. 2016, 138, 7194.

30) Nagorny, P.; Cichowicz, N. "New Strategy Based on Sequential Michael/Aldol Reactions for the Asymmetric Synthesis of Cardenolides" Strategies and Tactics in Organic Synthesis 12 (Book chapter), 2016, in production.

29) Khomutnyk, Y. Y.; Arguelles, A. J.; Winschel, G. A.; Sun, Z.; Zimmerman, P. M.;* Nagorny, P.* "Studies of the Mechanism and Origins of Enantioselectivity for the Chiral Phosphoric Acid-Catalyzed Stereoselective Spiroketalization" J. Am. Chem. Soc. 2016, 138, 444.

28) Cichowicz, N.; Kaplan, W.; Khomutnik, I.; Bhattarai, B.; Sun, Z.; Nagorny, P.* "Concise enantioselective synthesis of oxygenated steroids via sequential copper(II)-catalyzed Michael addition/intramolecular aldol cyclization reactions" J. Am. Chem. Soc. 2015, 137, 14341.

27) Tay, J.-H.; Nagorny, P.* "31P NMR-based Method for Determining Enantiopurity of Chiral Phosphoric Acids, and Its Application to the BINOL- and H8-BINOL-based Chiral Phosphoric Acid Thermal Racemization Studies" Synlett (Invited submission for Asymmetric Phosphoric Acid Catalysis Cluster) 2015,In Press, (DOI: 10.1055/s-0035-1560547).

26) Larsen, B. J.; Sun, Z.; Lachacz, E.; Khomutnik, I.; Soellner, M. B.; Nagorny, P.* "Synthesis and Biological Evaluation of Lactimidomycin and its Analogs" Chem. Eur. J. 2015, 21, 19159.

25) Tay, J.-H.; Arguelles, J. A.; Nagorny, P.* "Direct Interconversion of BINOL and H8-BINOL-based Chiral Bronsted Acids Using Single Step Red/Ox Manipulations" Org. Lett.2015, 17, 3774.

24) Bhattarai, B.; Tay, J.-H.; Nagorny, P.* "Thiophosphoramides as Cooperative Catalysts for Copper-Catalyzed Arylation of Carboxylates with Diaryliodonium Salts" Chem. Commun. 2015, 51, 5398.

23) Sun, Z.; Winschel, G. A.; Zimmerman, P.;* Nagorny, P.* "Enantioselective Synthesis of Piperidines through the Formation of Chiral Mixed Phosphoric Acid Acetals: Experimental and Theoretical Studies" Angew. Chem. Int. Ed. 2014, 53, 11194.

22) Borovika, A.; Tang, P.-I.; Klapman, S.; Nagorny, P.* "Thiophosphoramide-Based Cooperative Catalysts for the Bronsted Acid-Catalyzed Cyclization of Unsaturated Acetals" Angew. Chem. Int. Ed. 2013, 52, 13424-13428.

21) Mensah, E.; Camasso, N.; Kaplan, W.; Nagorny, P.* "Chiral Phosphoric Acid-Directed Regioselective Acetalization of Carbohydrate-Derived 1,2-diols" Angew. Chem. Int. Ed. 2013, 52, 13939-12-936.

20) Larsen, B.; Sun, Z.; Nagorny, P.* "Synthesis of Eukaryotic Translation Elongation Inhibitor Lactimidomycin via Zin(II)-mediated Horner-Wadswarth-Emmons Macrocyclization" Org. Lett. 2013, 15, 2998-3001.

19) Borovika, A.; Nagorny, P.* "Chiral Bronsted Acid–catalyzed Enantioselective Ionic [2+4] Cycloadditions" Tetrahedron (Special Edition dedicated to Prof. M. Sanford TYIA) 2013, 69, 5719-5725.

18) Nagorny, P.*, Sun, Z.; Winschel, G. "Chiral Phosphoric Acid Catalyzed Stereoselective spiroketalizations" Synlett (Invited Synpacts Article) 2013, 24, 661–665.

17) Sun, Z.; Winschel, G. A.; Borovika, A.; Nagorny, P.* "Chiral Phosphoric Acid–Catalyzed Enantioselective and Diastereoselective Spiroketalizations" J. Am. Chem. Soc. 2012, 134(19), 8074–8077.

16) Cichowicz, N.; Nagorny, P.* "Synthesis of Conjugated Polyenes via Sequential Condensation of Sulfonylphosphonates and Aldehydes" Org. Lett. 2012, 14(4), 1058–1061.

15) Borovika, A.; Nagorny, P.* "Recent Advances in the Synthesis of 2–deoxyglycosides" J. Carbohydr. Chem. (invited review) 2012, 31, 255–283.

Peer–Reviewed Publications from Postdoctoral, Graduate and Undergraduate Research:



14) Aussedat, B.; Fasching, B.; Johnston, E.; Sane, N.; Nagorny, P.; Danishefsky, S. J.* "Total Synthesis of the alpha–Subunit of Human Glycoprotein Hormones: Toward Fully Synthetic Homogeneous Human Follicle–Stimulating Hormone" J. Am. Chem. Soc. 2012, 134(7), 3532–3541.

13) Nagorny, P.;& Sane, N.;& Fasching, B.; Aussedat, B.; Danishefsky, S. J.* "Probing the Frontiers of Glycoprotein Synthesis: The Fully Elaborated beta–Subunit of the Human Follicle–Stimulating Hormone" Angew. Chem. Int. Ed. 2012, 51(4), 975–979. (&equally contributing authors).

12) Lecomte, N.; Njardarson, J.; Nagorny, P.; Yang, G.; Downey, R.; Ouerfelli, O.; Moore, M.; Danishefsky, S. J.* "Emergence of Potent Inhibitors of Metastasis in Lung Cancer via Syntheses Based on Migrastatin" Proc. Natl. Acad. Sci. USA 2011, 108, 15074–15078.

11) Nagorny, P.; Krauss, I.; Njardarson, J. T.; Perez, L.; Gaul, C.; Yang, G.; Ouerfelli, O.; Danishefsky, S. J.* "Confirmation of the structure of synthetic derivatives of migrastatin in the light of recently disclosed crystallographically based claims" Tetrahedron Lett. 2010, 51(30), 3873–3875.

10)
Oskarsson, T.; Nagorny, P.; Krauss, I. J.; Perez, L.; Mandal, M.; Yang, G.; Ouerfelli, O.; Xiao, D.; Moore, M. A. S.; Massague, J.; Danishefsky, S. J.* "Promising Cell-Migration Inhibitors for Treatment of Tumor Metastasis: In Vivo and Mechanistic Studies on the Migrastatin Core Ether Analogs" J. Am. Chem. Soc. 2010, 132(9), 3224–3228.

9) Rao, Y.; Li, X.; Nagorny, P.; Hayashi J.; Danishefsky, S. J.* "A Simple Method for the Conversion of Carboxylic Acids into Thioacids with Lawesson's Reagent" Tetrahedron Lett. 2009, 50(48), 6684–6686.

8) Nagorny, P.; Kim, W. H.; Wan, Q.; Lee, D.; Danishefsky, S. J.* On the Emerging Role of Chemistry in the Fashioning of Biologics: Synthesis of a Bidomainal Fucosyl GM1–Based Vaccine for the Treatment of Small Cell Lung Cancer" J. Org. Chem. 2009, 74(15), 5157–5162.

7) Nagorny, P.; Fasching, B.; Li, X.; Chen, G.; Aussedat, B.; Danishefsky, S. J.* Toward Fully Synthetic Homogeneous b–Human Follicle–Stimulating Hormone (b–hFSH) with a Biantennary N–Linked Dodecasaccharide. Synthesis of b–hFSH with Chitobiose Units at the Natural Linkage Sites J. Am. Chem. Soc. 2009, 131(16), 5792–5799.

6) Evans, D. A.*; Nagorny, P.; McRae, K. J.; Reynolds, D. J.; Sonntag, L.–S.; Vounatsos, F.; Xu, R. "Enantioselective Synthesis of Oasomycin A, Part I. Synthesis of the C1–C12 and C13–C28 Subunits" Angew. Chem. Int. Ed. 2007, 46, 537–540.

5) Evans, D. A.*; Nagorny, P.; Reynolds, D. J.; McRae, K. J. "Enantioselective Synthesis of Oasomycin A, Part II. Synthesis of the C29–C46 Subunit" Angew. Chem. Int. Ed. 2007, 46, 541–544.

4) Evans, D. A.*; Nagorny, P.; McRae, K. J.; Reynolds, D. J.; Sonntag, L.–S.; Vounatsos, F.; Xu, R. "Enantioselective Synthesis of Oasomycin A, Part III. Fragment Assembly and Conformation of Structure" Angew. Chem. Int. Ed. 2007, 46, 545–548.

3) Evans, D. A.*; Nagorny, P.; Xu, R. "Ceric Ammonium Nitrate Promoted Oxidation of Oxazoles" Org. Lett. 2006, 8, 5669–5671.

2) Blakemore, P.R.; Browder, C.C.; Hong, J.; Lincoln, C.M.; Nagornyy, P.A.; Robage, L.A.; Wardrop, D.J.; White, J.D.* Total Synthesis of Polycavernoside A, A Lethal Toxin of the Red Alga Polycavernosa tsudai" J. Org. Chem. 2005, 70, 5449–5460.

1) White, J.D.*; Blakemore, P.R.; Browder, C.C.; Hong, J.; Lincoln, C.M.; Nagornyy, P.A.; Robage, L.A.; Wardrop, D.J. Total Synthesis of the Marine Toxin Polycavernoside A via Selective Macrolactonization of a Trihydroxy Carboxylic Acid" J. Am. Chem. Soc. 2001, 123, 8593–8595.

Patents:


Nagorny, P.; Arguelles, A.; Sun, S. Spiroketal-Based C2-Symmetric Scaffold for Asymmetric Catalysis. U.S. Patent No. 10,565,015 (February 18, 2020).


Invited Presentations (University of Michigan):

 

08/18/2020 - ACS 2020 National Symposium, San Francisco (Invited Presentation at "Modern Catalytic Methods for the Preparation and Functionalization of Carbohydrates"  

06/16/2020  - NIH Common Fund Glycoscience Virtual Meeting (Open Session Talk)

01/09/2020  - Massachusetts Institute of Technology

06/24/2019  - Carbohydrates Gordon Research Conference, Hong Kong (short talk)

06/21/2019  - Hong Kong University of Science and Technology

06/08/2019 – The 50th ACS Central Regional Meeting at Midland

09/12/2018 –  24th Conference on Isoprenoids, Bialystok, Poland

06/16/2018 – Glass City Chemistry Conference, Session on the Synthesis of Biologically Active Compounds, University of Toledo

03/19/2018 – ACS National Meeting, New Orleans, (Invited Presentation at “Recent Advances in Catalytic Carbohydrate Reaction Development”)

08/31/2017 – NIH CFG Program Principal Investigator Meeting

08/22/2017 – University of Toronto

5/22/2017 –Dow AgroSciences LLC (Indianapolis)

3/1/2017 –Bristol-Myers-Squib (Invited presentations at the Discovery and Process Sites at Lawrenceville, New Brunswick and Wallingford)

10/14/2016 –12th Annual Midwest Carbohydrate and Glycobiology Symposium (at Central Michigan University)

9/19/2016 –University of Michigan (promotion seminar)

5/20/2016 – The 47th ACS CERM at Cincinnati, Synthetic Organic Methods and Total Synthesis Session

4/22/2016 – University of Minnesota

3/14/2016 – Rice University

3/4/2016 – Vanderbilt University

3/3/2016 – University of North Carolina at Chapel Hill

2/29/2016 – Princeton University

2/26/2016 – University of Chicago

12/08/2015 – UC Berkeley

11/13/2015 – Brandeis University

11/11/2015 – Dartmouth College

11/4/2015 – California Institute of Technology

10/29/2015 – Cornell University

10/27/2015 – Memorial Sloan-Kettering Cancer Center

10/21/2015 – Wayne State University

10/16/2015 – University of Texas at Austin

10/14/2015 – Amgen Young Investigator's Symposium (Cambridge, MA)

10/8/2015 – University of California at Los Angeles

10/7/2015 – University of California at Irvine

10/6/2015 – University of California at Santa Barbara

9/29/2015 – Purdue University

9/21/2015 – Indiana University

8/31/2015 – Boehringer Ingelheim

6/21/2015 – GRC Heterocyclic Compounds
3/18/2015 – Michigan State University
1/30/2015 – University of Texas at San Antonio
11/20/2014 – Oregon State University
10/29/2014 – The 45th ACS Central Regional Meeting at Pittsburg, Synthetic Organic Methods and Total Synthesis Session
9/19/2014 – University of Michigan, Dearborn

8/11/2014 – 248th ACS National Meeting, Younger Investigator National Awardee Forum: Emerging Frontiers in Chemistry Research

8/10/2014 –248th ACS National Meeting, Young Academic Investigators Award Symposium

7/25/2014 – Gordon Research Conference "Natural Products", short talk

4/21/2014 – Western Michigan University

3/28/2014 – CBI Symposium, University of Michigan
4/11/2013 – University of Toledo, College of Pharmacy
10/5/2012 – 8th Midwest Carbohydrate and Glycobiology Symposium (Invited Lecture, Wayne State University)
8/1/2012 – Gordon Research Conference (Stereochemistry), Chalk Talk and Poster Presentation
7/26/2012 – Gordon Research Conference (Natural Products), Poster Presentation
11/16/2011 – Oakland University
5/16/2011 – NIH Mentoring workshop
11/18/2010 – University of Michigan, Medicinal Chemistry Seminar Series

Invited Seminars (Postdoctoral):



2010 – Princeton University
2010 – Stony Brook University
2010 – California Institute of Technology
2010 – University of Texas, Medical Branch at Galveston
2009 – Wayne State University
2009 – University of North Carolina, Greensboro
2009 – University of Michigan