Research in our group is focused on (i) design of new steroid and terpenoid-based agents for the treatment of human diseases; (ii) development of non-enzymatic catalytic processes for the regio- and stereoselective assembly of oligosaccharides and glycoconjugates; (iii) discovery of new organic transformations and processes that could improve the accessibility of bioactive natural products and therapeutic agents. In particular, our group is interested in exploring organic catalysts to accomplish selective transformations that are typically believed to proceed through the intermediacy of oxocarbenium ions. While a number of important transformations could proceed through these reactive intermediates, harnessing the reactivity of oxocarbeniums through catalysis represents a challenging task. Our group has discovered that chiral Brønsted acids could serve as effective catalysts for controlling stereo- and regioselective reactions of saturated and unsaturated oxocarbeniums. Our current efforts are focused on further exploring the scope of such transformations, understanding the origins of selectivity and rationally designing new catalysts with superior properties.
1) Borovika, A.; Tang, P.-I.; Nagorny, P.* “Thiophosphoramide-Based Cooperative Catalysts for the Brønsted Acid-Promoted Ionic Diels-Alder Reactions” Angew. Chem. Int. Ed. 2013, 52, 13424.
• Selected as the “Hot Paper” by the editorial office of ACIEE
• Highlighted in Synfacts 2014, 10(1), 90.
2) Mensah, E.; Camasso, N.; Nagorny, P.* “Chiral Phosphoric Acid-Directed Regioselective Acetalization of Carbohydrate-Derived 1,2-diols” Angew. Chem. Int. Ed. 2013, 52, 12932.
• Selected for F1000Prime as an article of special significance
3) Larsen, B.; Sun, Z.; Nagorny, P.* “Synthesis of Eukaryotic Translation Elongation Inhibitor Lactimidomycin via Zn(II)-mediated Horner-Wadsworth-Emmons Macrocyclization” Org. Lett. 2013, 15, 2998-3001.
4) Borovika, A.; Nagorny, P.* “Chiral Brønsted Acid-catalyzed Enantioselective Ionic [2+4] Cycloadditions” Tetrahedron (Special Edition dedicated to Prof. M. Sanford TYIA) 2013, 69, 5719-5725.
• Highlighted in ChemInform 2013, 44(45), (DOI: 10.1002/chin.201345025)
5) Nagorny, P.*, Sun, Z.; Winschel, G. “Chiral Phosphoric Acid Catalyzed Stereoselective spiroketalizations” Synlett (Invited Synpacts Article) 2013, 24, 661-665.
6) 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.
• Highlighted in Synfacts 2012, 8(7), 0794; and ChemInform 2012, 43(40), (DOI: 10.1002/chin.201240117)
7) Cichowicz, N.; Nagorny, P.* “Synthesis of Conjugated Polyenes via Sequential Condensation of Sulfonylphosphonates and Aldehydes” Org. Lett. 2012, 14(4), 1058-1061.
• Highlighted in Comprehensive Organic Synthesis (“Olefination of Carbonyl Compounds by Main-group Element Mediators”, 2nd Edition, In Production).
8) Borovika, A.; Nagorny, P.* “Recent Advances in the Synthesis of b-2-deoxyglycosides” J. Carbohydr. Chem. (invited review) 2012, 31, 255-283.
• Highlighted in ChemInform 2012, 43(45), DOI: 10.1002/chin.201245245 (one of the most downloaded articles of the Journal of Carbohydrate Chemistry).
Peer-Reviewed Publications from Postdoctoral, Graduate and Undergraduate Research:
9) 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.
10) 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).