Gordon Wayne Gribble
Professor of ChemistryThe Dartmouth Professor of Chemistry
Professor Gribble's research program covers several areas of organic chemistry, most of which involve synthesis, including novel indole chemistry, triterpenoid synthesis, DNA intercalation, and new synthetic methodology. Of prime interest is the synthesis of bis-acridines that act as DNA double intercalators, one of which is active against human glioblastoma cells. In the area of new synthetic methodology, Dr. Gribble and his students have discovered new chemistry of nitroindoles. A third area of research is the synthesis and biological activity of triterpenoids in the chemoprevention of cancer and other diseases related to inflammation. One of these synthetic triterpenoids, "bardoxolone methyl" has entered Phase 3 clinical trials for the treatment of chronic kidney disease in diabetes patients.
Dr. Gribble also has a deep interest in naturally occurring organohalogen compounds, and in the chemistry of wine and wine making.
“Potential DNA Bis-Intercalating Agents. Synthesis and Antitumor Activity of N,N-Methylenedi-4,1-cyclohexanediyl-bis(9-acridinamine) Isomers”; Gribble, G.W.; Mosher, M.D.; Jaycox, G.D.; Cory, M.; Fairley, T.A. Heterocycles, 2014, 88, 535-546.
“Synthesis and Biological Evaluation of Amino Acid Methyl Ester Conjugates of 2-Cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid Against the Production of Nitric Oxide (NO)”; Onyango, E.O.; Fu, L.; Cao, M.; Liby, K.T.; Sporn, M.B.; Gribble, G.W. Bioorg. Med. Chem. Lett. 2014, 24, 532-534.
“Synthesis of a Dicyano Abietane, a Key Intermediate for the Antiinflammatory Agent ‘TBE-31’”; Onyango, E.O.; Fu, L.; Gribble, G.W. Organic Lett. 2014, 16, 322-324.
“The Reaction of Arynes with Münchnones: Synthesis of Isoindoles and Azaisoindoles”; Lopchuk, J.M; Gribble, G.W. Tetrahedron Lett. 2014, 55, 2809-2812.
“An Efficient Synthesis of Methyl 2-Cyano-3,12-dioxoursol-1,9-dien-28-oate (CDDU-Methyl Ester); Analogues, Biological Activities, and Comparison with Oleanolic Acid Derivatives”; Fu, L.; Lin, Q.-X.; Liby, K.T.; Sporn, M.B.; Gribble, G.W. Org. Biomol. Chem. 2014, 12, 5192-5200.
“Synthesis of a Furano Abietane Cyano Enone – A New Scaffold for Biological Exploration”; Onyango, E.O.; Fu, L.; Gribble, G.W. Tetrahedron Lett. 2014, 55, 4636-4638.
“Fluorinated Imidazoles and Benzimidazoles”; Gribble, G.W.; Roy, S.; Roy, S. In Fluorine in Heterocyclic Chemistry Volume 1: 5-Membered Heterocycles and Macrocycles; Nenajdenko, V., Ed.; Springer, Berlin, 2014, 323-367.
“Total Synthesis of Atorvastatin via a Late-Stage, Regioselective 1,3-Dipolar Münchnone Cycloaddition”; Lopchuk, J.M; Gribble, G.W. Tetrahedron Lett. 2015, 56, in press (Invited for the Henry Wasserman Special Issue).
"Synthesis of Heteraryl-Substituted Pyrroles via the 1,3-Dipolar Cycloaddition of Unsymmetrical Münchnones and Nitrovinyl Heterocycles"; Lopchuk, J.M.; Song, M.; Butler, B.; Gribble, G.W. Synthesis, 2015, in press (Invited for a Special Issue on Cycloaddition Reactions and Methods).
"A Recent Survery of Naturally Occuring Organhalogen Compounds"; Gribble, G.W., Environ. Chem. 2015, 12, 396-405 (Special Issue on "Natural Halogenation).
"Novel Synthesis of 1-Bromo-8-methylnaphthalene and 1-Bromo-45 methylnaphthalene"; Onyango, E.O.; Kelley, A.R.; Qian, D.C.; Gribble, G.W. J. Org. Chem. 2015, 80, 5970-5972.
"Biological Activity of Recently Discovered Halogenated Marine Natural Products"; Gribble, G.W. Marine Drugs, 2015, 13, 4044-4136.
"Novel Synthetic Pyridyl Analogues of CDDO-Imidazolide Are Useful New Tools in Cancer Prevention"; Cao, M.; Onyango, E.O.; Williams, C.R.; Royce, D.B.; Gribble, G.W.; Sporn, M.B. Liby, K.T. Pharmacol. Res., 2015, 100, 135-147.
Works in Progress
“Naturally Occurring Organohalogen Compounds — A Comprehensive Update”
“Indole Ring Synthesis: From Natural Products to Drug Discovery”
“Captain Aaron Gove Wilkins ’1942 – Iwo Jima Marine Corps Hero”