Gordon Wayne Gribble

Academic Appointments

Professor of Chemistry Emeritus
The Dartmouth Professor of Chemistry Emeritus
Research 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.

+ View more

Contact

Gordon.W.Gribble@Dartmouth.EDU

8023564284

313 Burke

Department(s)

Chemistry

Education

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.
"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, 55, 2168-2171.
"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.
"Synthesis of Bis-4H-furo[3,4-b]indoles"; McGowan, M.A.; Perreault, D.M.; Thornton, N.B.; Garaas, S.D.; Gribble, G.W. Arkivoc 2018, v, 334-347.
"The Synthesis of (±)-1,2,3,4,6,7,12,12b-Octahydroindolo[2,3-b]quinolizine from Tryptophan and Dihydropyran"; Badenock, J.C.; Gribble, G.W. Org. Prep. & Proc. Internat. 2018, 50, 449-453.
"Modified ToxT Inhibitor Reduces Vibrio cholera Virulence In Vivo"; Woodbrey, A.K.; Onyango, E.O.; Kovacikova, G.; Kull, J.F.; Gribble, G.W. Biochemistry 2018, 57, 5609-5615.
"Synthesis and Cytotoxicity of New Bis-Ellipticines and Bis-Isoellipticines"; Obaza-Nutaitis, J.A.; Gribble, G.W. Heterocycles 2019, 99, DOI: 10.3987/COM-18-S(F)6.
"Synthesis and DNA Binding of 6-(Alkylamino)indolo[1,2-b][2,7]naphthyridine-5,12-quinones"; Davis, D.A.; Cory, M.; Fairley, T.A.; Gribble, G.W. Arkivoc 2019, iii, 53-66.
"Synthetic Studies Towards N-Substituted 3-Vinyl-4-piperidineacetic Acid Derivatives"; Johnson, D.A.; Gribble, G.W. Arkivoc 2019, v, 178-195.
"Synthesis of Pyrrolo[1,2-c]pyrimidines"; Narayan, E.; Fu, L.; Gribble, G.W Heterocycles, 2021, 103, 476-483, for a Special issue in Honor of Professor Yasuyuki Kita.
"4-Fluoro-5-methylacridine: In Search of Long-Range "Lone-Pair Mediated" H-F and C-F Spin-Spin Coupling"; Olson, E. R.; Gribble, G.W. Org. Prep. Proc. Int. 2021, 53, 100-104.
"Synthesis of New Pyrrolo[3,4-b]indol-3-ones as Latent Substrates for Pyrrolo[3,4-b]indoles"; Saulnier, M.G.; Schreiber, S.M.; Cavanaugh, K.L.; Perni, R.B.; Joyner, H.H.; Gribble, G.W. Arkivoc 2021, v, 15-23.
"A Simple Synthesis of a Pillar[n]arene Building Block – 1,4-bis(4-Bromobenzyl)benzene"; Nutaitis, C.F.; Gribble, G.W. Org. Prep. Proc. Int. 2021, 53, 422-425.
"Concerning a Preparation of 6-Bromotryptamine"; Wiens, P.S.: Johnson, J.L.; Gribble, G.W. Tetrahedron 2021, 85, 132035.
"Recent Discoveries of Naturally Occurring Halogenated Nitrogen Heterocycles"; Gribble, G.W. Prog. Heterocycl. Chem. 2021, 33, 1-26.
"Naturally Occurring Organohalogen Compounds — A Comprehensive Survey"; Gribble, G.W. Progress in the Chemistry of Organic Natural Products, 2023, 121, in production
"2-Bromo-1-(phenylsulfonyl)-1H-indol-3-yl Trifluoromethanesulfonate "; Wright, S.W.; Gribble, G.W. Org. Prep. Proc. Int. 2023, in press.

+ View more

Works In Progress

"Indole Ring Synthesis: From Natural Products to Drug Discovery"
"Captain Aaron Gove Wilkins '1942 – Iwo Jima Marine Corps Hero"

Admissions

Academics

Campus Life

More

Arts & Sciences Faculty

Dartmouth Directory
Arts & Sciences Faculty

Gordon Wayne Gribble

Professor of Chemistry Emeritus

The Dartmouth Professor of Chemistry Emeritus

Research Professor of Chemistry

Contact

Department(s)

Education

Selected Publications

Works In Progress

Gordon Wayne Gribble

Professor of Chemistry Emeritus

The Dartmouth Professor of Chemistry Emeritus

Research Professor of Chemistry

Contact

Department(s)

Education

Selected Publications

Works In Progress

Related Links