Gordon Wayne Gribble

Professor of Chemistry
The 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.

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Dr. Gribble also has a deep interest in naturally occurring organohalogen compounds, and in the chemistry of wine and wine making.

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313 Burke
HB 6128
A.A. San Francisco City College
B.S. University of California at Berkeley
Ph.D. University of Oregon

Selected Publications

“Total Synthesis of Atorvastatin via a Late-Stage, Regioselective 1,3-Dipolar Münchnone Cycloaddition”; Lopchuk, J.M; Gribble, G.W. Tetrahedron Lett. 2015, 56, 3208-3211 (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, 47, 2776-2780 (Invited for a Special Issue on Cycloaddition Reactions and Methods).

“A Recent Survey of Naturally Occurring Organohalogen 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.

“Synthesis, Crystal Structures and DFT Calculations of Three New Cyano(phenylsulfonyl)indoles and a Key Synthetic Precursor Compound”; Montgomery, W.L.; Lopchuk, J.M.; Gribble, G.W.; Jasinski, J.P. Crystals, 2015, 5, 376-393.

“Triple Benzannulation of Naphthalene via a 1,3,6-Naphthotriyne Synthetic Equivalent. Synthesis of Dibenz[a,c]anthracene”; Mannes, P.Z.; Onyango, E.O.; Gribble, G.W. J. Org. Chem. 2015, 80, 11189-11192.

“Synthesis of a Monofluoro 3-Alkyl-2-hydroxy-1,4-naphthoquinone: A Potential Anti-Malarial Drug”; Kim, E.E.; Onyango, E.O.; Fu, L.; Gribble, G.W. Tetrahedron Lett. 2015, 56, 6707-6710.

“What Ever Happened to Dioxin? An Update on the “Doomsday Chemical” of the 1970s and 1980s”; Gribble, G.W. Priorities 2016, March, 11-13.

“Three-Component Reductive Alkylation of 2-Hydroxy-1,4-naphthoquinones with Lactols”; Kim, E.E.; Onyango, E.O.; Pace, J.R.; Abbot, T.M.; Fu, L.; Gribble, G.W. Tetrahedron Lett. 2016, 57, 864-867.

“Metal-Catalyzed Coupling with Heterocycles”; Badenock, J.C.; Gribble, G.W. Advances in Heterocyclic Chemistry 2016, 120, 99-136.

“Indole Ring Synthesis – From Natural Products to Drug Discovery”; Gribble, G.W.; John Wiley & Sons, Chichester, UK, 2016.

"Six-Membered Ring Systems:  Pyridine and Benzo Derivatives"; Gribble, G.W.; Kishbaugh, T.L.S. Prog. Heterocycl. Chem. 2016, 28, 391-437.

“Synthesis of a Masked 2,3-Diaminoindole”; Mannes, P.Z.; Onyango, E.O.; Gribble, G.W. J. Org. Chem. 2016, 81, 12478-12481.


"tert-Butyl 2,3-Dihydro-1H-cyclopenta[b]indole-4-carboxylate"; Jordan, J.A.; Badenock, J.C.; Gribble, G.W.; Kaur, M.; Jasinski, J.P. IUCrDATA 2016, 1, 161468.

“What Ever Happened to Dioxin?  An Update on the “Doomsday Chemical” of the 1970s and 1980s”; Gribble, G.W. Priorities 2016, March, 11-13.

"Synthesis, Crystal Structures, and DFT Calculations of Three Novel 1-(Phenylsulfonyl)indoles"; Mannes, P.Z.; Kaur, M.; Onyango, E.O.; Gribble, G.W.; Jasinski, J.P. J. Chem. Crystallogr. 2017, 47, 10-21.

“Photo-degradation of 2,4-Dinitroanisole (DNAN):  An Emerging Munitions Compound”; Taylor, S.; Walsh, M.E.; Becher, J.B.; Ringelberg, D.B.; Mannes, P.Z.; Gribble, G.W. Chemosphere 2017, 167, 193-203.

“A New Class of Inhibitors of the AraC Family of Virulence Regulator Vibrio cholera ToxT”; Kelley, A.R.; Onyango, E.O.; Pellegrini, M.; Kovacikova, G.; Taylor, R.K.; Gribble, G.W.; Kull, J.F. Scientific Reports 2017, 7, 45011.


 “Design, Synthesis, and Biological Activity of Second-Generation Synthetic Oleanane Triterpenoids”; Fu, L.; Lin, Q.; Onyango, E.O.; Liby, K.T.; Sporn, M.B.; Gribble, G.W. Org. Biomol. Chem. 2017, 15, 6001-6005.

“The Synthesis of 7,8,9,10-Tetrafluoroellipticine”; Gruver, E.J.; Onyango, E.O.; Gribble, G.W. Arkivoc 2018, iii, 144-152.

“Synthesis of 6-Oxo-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-b]quinolizine”; Tompkins, D.C.; Reilly, Jr., L.W.; Nelson, R.B.; Dolby, L.J.; Gribble, G.W. J. Heterocycl. Chem. 2018, 55, 1048-1052.

“A Short Synthesis of 9-Fluoroellipticine”; Davis, D.A; Gribble, G.W. Heterocycles 2018, DOI:10.3987/COM-18-S(T)30.


“A Synthetic Approach to (±)-Aristomakine”; Perni, R. B.; Gribble, G.W. Arkivoc 2018, iv, 75-84.

“A New Approach to the Pyrrolo[3,4-b]indole Ring System”; Badenock, J.C.; Gribble, G.W. Arkivoc 2018, v, 140-149.

            “Synthesis of 7-Oxo-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-b]quinolizine”; Tompkins, D.C.; Nelson, R.B.; Dolby, L.J.; Gribble, G.W. J. Heterocycl. Chem. 2018, DOI 10.1002/jhet.3251

“Synthesis and Cytotoxicity of New Bis-Ellipticines and Bis-Isoellipticines”; Obaza-Nutaitis, J.A.; Gribble, G.W. Heterocycles 2018, DOI: 10.3987/COM-18-S(F)6.


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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”