Dr. John Gupton III
Professor of Chemistry
C-309 Gottwald Center for the Sciences
Office: (804) 287-6498
Fax: (804) 287-1897
http://facultystaff.richmond.edu/~jgupton
Speciality:
Organic Chemistry
Teaching:
Organic Chemistry I Lecture & Lab
Research:
Dr. Gupton's primary research interests involve developing new organic reactions that can be applied to the synthesis of bioactive compounds in agriculture and medicine. More specifically, he has studied for some time the preparation and reactions of novel vinylogous iminium salts as building blocks for the construction of highly functionalized heterocycles. In recent years this work has focused on the preparation of pyrroles by this methodolgy and the subsequent application to the synthesis of bioactive marine natural products which contain the pyrrole ring system.
Education:
Ph.D., Georgia Institute of Technology
Selected Publications:
J. Gupton, S. Clough, C. Hickenboth*, I. Bluhn Chertudi*, S. Cutro*, S. Petrich, F. Hicks*, D. Wilkinson* and J. Sikorski, "The Application of Vinylogous Iminium Salt Derivatives to the Regiocontrolled Preparation of Heterocyclic Appended Pyrazoles", Tetrahedron, 58, 5467-5474 (2002).
J. Gupton, S. Clough, R. Miller, J. Lukens*, C. Henry*, R. Kanters and J. Sikorski, "The Application of Vinylogous Iminium Salt Derivatives to the Synthesis of Ningaline B Hexamethyl Ether", Tetrahedron, 59, 207-215 (2003).
H. Yamanaka, K. Kase, M. Katayama, T. Ishihara, T. Konno and J. Gupton, "Reaction of ß-Trifluoroethoxy Vinamidinium Salts with Carbon Nucleophiles", J. of Fluorine Chem., 120, 33-39 (2003).
B. Burnham, M. Evans, D. Smith, J. Holub, A. Argenti, M. Hoff, G. Daglish, D. Wilson, B. Taylor, J. Berkowitz, K. Krumpe, J. Gupton, T. Scarleet, R. Durham and I. Hall, "Synthesis and Cytotoxicity of Substituted Ethyl-2-Phenacyl-3-phenylpyrrole-4-carboxylates", Arch. Pharm. Pharm. Med. Chem., 336, 181-190 (2003).
S. Clough, J. Gupton, K. Griffin*, A. Hewitt*, M. Hudson*, A. Ligali*, S. Mulcahey*, M. Roberts*, R. Miller and B. Norwood, "Extension of ß-Chloroenals to Ethyl 5-Chloro-2,4-pentadienoates Using Wadsworth-Emmons Reactions: Subsequent Conversions to 5-Aryl-5-chloro-2,4-pentadienoic Acids and 5-Aryl-2-penten-4-ynoic Acids", Tetrahedron, 60, 10165-10169 (2004).
J. Gupton, R. Miller, S. Clough, K. Krumpe, E. Banner, R. Kanters, K. Du, K. Keertikar, N. Lauerman*, J. Solano*, B. Adams*, D. Callahan*, B. Little*, A. Scharf*, and J. Sikorski, "The Application of Vinylogous Iminium Salt Derivatives to an Efficient Relay Synthesis of the Pyrrole Containing Alkaloids Polycitone A and B", Tetrahedron, 61, 1845-1854 (2005).
S. Clough, J. Gupton, A. Ligali*, M. Roberts*, D. Driscoll*, S. Annett*, A. Hewitt*, M. Hudson*, E. Jackson*, R. Miller, B. Norwood, R. Kanters, H. Wyre* and H. Petruzzi*, "Reactions of (Z)-3-Aryl-3-chloropropenals with Nucleophiles: Stereoselective Formation of (E)-Vinylogous Esters, (E)-Vinylogous Amides and Vinamidinium Salts", Tetrahedron, 61, 7554-7561 (2005).
J. Gupton, “Pyrrole Natural Products with Antitumor Properties”, Chapter. 2, pp 53-92 in “Heterocyclic Antitumor Antibiotics: Topics in Heterocyclic Chemistry, Vol.2”, Ed. by M. Lee, Springer-Verlag, Berlin/Heidelberg, 2006: ISBN # 3-540-30982-9.
J. Gupton, E. Banner, A. Scharf*, B. Norwood, R. Kanters, R. Dominey, J. Hempel*, A. Kharlamova*, I. Bluhn-Chertudi*, C. Hickenboth*, B. Little*, M. Coppock*, K. Krumpe, B. Burnham, H. Holt., K. Du, K. Keertikar, A. Diebes, S. Ghassemi and J. Sikorski, “The Application of Vinylogous Iminium Salt Derivatives to an Efficient Synthesis of the Pyrrole Containing Alkaloids Rigidin and Rigidin E”, Tetrahedron, 62, 8243-8255 (2006).
S. Arimitsu, T. Konno, T. Ishihara, H. Yamanaka and J. Gupton, “Synthetic Application of Fluorinated Vinamidinium Salts: Synthesis of Fluorinated 1,3-butadienylphosphonates by the Reaction With Horner-Wadsworth-Emmons Reagents”, J. of Fluorine Chem., 127, 1235-1241 (2006).
S. Mooberry, K. Wiederhold, S. Dakshanamurthy, E. Hamel, E. Banner, A. Kharlamova*, J. Hempel*, J. Gupton and M. Brown, “Identification and Characterization of a New Tubulin-Binding Tetrasubstituted Brominated Pyrrole”, Molecular Pharmacology, 72 (1), 132-140 (2007).
C. Arthur, J. Gupton, G. Kellog, A. Yeudall and D. Gewirtz, “Autophagic Cell Death, Polyploidy and Senescence Induced in Breast Tumor Cells by the Substituted Pyrrole JG-03-14, a Novel Microtubule Poison”, Biochemical Pharmacology, 74, 981-991 (2007).
A. Tripathi, M. Fornabaio, G. Kellogg, J. Gupton, D. Gewirtz, W. Yeudall, N. Vega and S. Mooberry, “Docking and Hydropathic Scoring of Polysubstituted Pyrrole Compounds with Anti-Tubulin Activity”, Biorganic and Medicinal Chemistry, 16, #5, 2235-2242 (2008).
J. Gupton, E. Banner, M. Sartin*, M. Coppock*, J. Hempel*, A. Kharlamova*, D. Fisher*, B. Giglio*, K. Smith*, M. Keough*, T. Smith, R. Kanters, R. Dominey and J. Sikorski, “Application of Vinylogous Iminium Salt Derivatives and Microwave Accelerated Vilsmeier-Haack Reactions to Efficient Relay Syntheses of the Polycitone and Storniamide Natural Products”, Tetrahedron, 64, 5246-5243 (2008).
J. Gupton, B. Giglio*, J. Eaton*, E. Rieck*, K. Smith*, M. Keough*, P. Barelli*, L. Firich*, J. Hempel*,T. Smith and R. Kanters, R., “The Application of Vinylogous Iminium Salt Derivatives to Efficient Formal Syntheses of the Marine Alkaloids Lamellarin G trimethylether and Ningalin B”, Tetrahedron,65, 4283-4292 (2009).
N. Dalyot-Herman, F. Delgado-Lopez, D. Gewirtz, J. Gupton and E. Schwartz, “Interference with Endothelial Cell Function by JG-03-14, an Agent That Binds to the Colchicine Site on Microtubules”, Biochemical Pharmacology, 78 (9), 1167-1177 (2009).
*Denotes undergraduate student co-authors
