Gordon W. Gribble

Professor Gribble received his B.S. degree in Chemistry in 1963 from the University of California, Berkeley, and his Ph.D. in Organic Chemistry in 1967 from the University of Oregon. After spending a year at UCLA as a National Cancer Institute Postdoctoral Fellow, he joined the faculty of Dartmouth College in 1968. Dr. Gribble has been a National Institutes of Health Research Career Development Awardee (1971-76), a National Science Foundation Professional Development Awardee (1977-78), and an American Cyanamid Academic Achievement Awardee (1988). In 2005 he was named to the endowed Chair “The Dartmouth Professor of Chemistry.” He is the co-editor of “Progress in Heterocyclic Chemistry” and the co-author of “Palladium in Heterocyclic Chemistry.”

Position: Dartmouth Professor of Chemistry
E-Mail: Gordon W. Gribble
Research Group Web Site

Research Interests

Professor Gribble's research programs involve several areas of organic chemistry, most of which involve synthesis: biologically active natural products, novel indole chemistry, anticancer triterpenoid synthesis, new synthetic methodology, and novel radical and cycloaddition chemistry of heterocycles. Of prime interest is the synthesis of plant indole alkaloids that are potent anticancer or antibiotic agents. Current work in this area is focused on ellipticine, vobasine, marine alkaloids, indolocarbazoles, and the zwitterionic alkaloids such as sempervirine. Thus, for example, several years ago Dr. Gribble developed a highly efficient synthesis of ellipticine, a derivative of which is currently used to treat several forms of human cancer. In the area of new synthetic methodology, Dr. Gribble and his students have been investigating the chemistry of nitroindoles. A newer area of research is the synthesis and biological activity of triterpenoids in the chemoprevention of cancer and diseases related to inflammation. Two of these synthetic triterpenoids are currently in Phase 1 clinical trials for the treatment of cancer.

Selected Publications

• “Nucleophilic Addition of Hetaryllithium Compounds to 3-Nitro-1-(phenylsulfonyl)indole:  Synthesis of Tetracyclic Thieno[3,2-c]-g-carbolines”; Alford, P.E.; Kishbaugh, T.L.S.; Gribble, G.W. Heterocycles 2009, xxx, xxx.w
• "Structures of Three New (Phenylsulfonyl)indole Derivatives"; Jasinski, J.P.; Rinderspacher, A.; Gribble, G.W. J. Chem. Crystallogr. 2009, xxx, xxx.
• "Probing Binding Determinants in Center P of the Cytochrome bc₁ Complex using Novel Hydroxynaphthoquinones"; Hughes, L.M.; Covian, R.; Gribble, G.W.; Trumpower, B.L. Biochim. Biophys. Acta – Bioenergetics 2009, xxx, xxx-xxx.
• "Naturally Occurring Organohalogen Compounds — A Comprehensive Survey"; Gribble, G.W. Progress in the Chemistry of Organic Natural Products, 2009, in press.
• "Hofmann Rearrangement"; Gribble, G.W., In Name Reactions for Homologations, Part II; Li, J. J., Ed.; John Wiley & Sons: Hoboken, New Jersey, 2009, 164-199.
• "Parham Cyclization"; Gribble, G.W., In Name Reactions for Homologations, Part II; Li, J. J., Ed.; John Wiley & Sons: Hoboken, New Jersey, 2009, 749-764.
• "Glaser Coupling"; Gribble, G.W., In Name Reactions for Homologations, Part I; Li, J. J., Ed.; John Wiley & Sons: Hoboken, New Jersey, 2009, 236-257.
• "A Short Synthesis of the Naturally Occurring Heptachloro- (Q1) and Heptabromo-1’-methyl-1,2’-bipyrroles"; Fu, L.; Gribble, G.W. Org. Prep. Proc. Int. 2008, 40, 561-566.
• "A Simple Synthesis of 2,2’-Bipyrroles from Pyrrole"; Fu, L.; Gribble, G.W. Tetrahedron Lett. 2008, 49, 7352-7354.
• "Mn(III)-Based Radical Addition Reactions of 2-Nitroindole with Activated CH Compounds"; Androsov, D.A.; Kishbaugh, T.L.S.; Gribble, G.W. Tetrahedron Lett. 2008, 49, 6621-6623.
• "A Novel Acetylenic Tricyclic Bis-(Cyanoenone) Potently Induces Phase 2 Cytoprotective Pathways and Blocks Liver Carcinogenesis Induced by Aflatoxin "; Liby, K.; Yore, M.M.; Roebuck, B.D.; Baumgartner, K.J.; Honda, T.; Sundararajan, C.; Yoshizawa, H.; Gribble, G.W.; Williams, C.R.; Risingsong, R.; Royce, D.B.; Dinkova-Kostova, A.T.; Stephenson, K.K.; Egner, P.A.; Yates, M.S.; Groopman, J.D.; Kensler, T.W.; Sporn, M.B. Cancer Res. 2008, 68, 6727-6733.
• “Prevention and Treatment of Experimental Estrogen Receptor-Negative Mammary Carcinogenesis by the Synthetic Triterpenoid CDDO-Methyl Ester and the Rexinoid LG100268”; Liby, K.; Risingsong, R.; Royce, D.B.; Williams, C.R.; Yore, M.M.; Honda, T.; Gribble, G W.; Lamph, W.W.; Vannini, N.; Sogno, I.; Albini, A.; Sporn, M.B. Clin. Cancer Res. 2008, 14, 4556-4563.
• "The Rexinoid LG100268 and the Synthetic Triterpenoid CDDO-Methyl Amide Are More Potent than Erlotinib for Prevention of Mouse Lung Carcinogenesis "; Liby, K.; Black, C.C.; Royce, D.B.; Williams, C.R.; Risingsong, R.; Yore, M.M.; Liu, X.; Honda, T.; Gribble, G.W.; Lamph, W.W.; Sporn, T.A.; Dmitrovsky, E.; Sporn, M.B. Mol. Cancer Ther. 2008, 7, 1251-1257.
• "Synthesis of 1,2’- and 1,3’-Bipyrroles from 2- and 3-Nitropyrroles"; Fu, L.; Gribble, G.W. Tetrahedron Lett. 2008, 49, 3545-3548.
• "The Synthetic Triterpenoid 2-Cyano-3,12-dioxooleana-1,9-dien-28-oic Acid-Imidazolide Alters Transforming Growth Factor b -dependent Signaling and Cell Migration by Affecting the Cytoskeleton and the Polarity Complex”; To, C.; Kulkarni, S.; Pawson, T.; Honda, T.; Gribble, G.W.; Sporn, M.B.; Wrana, J.L.; Di Guglielmo, G.M. J. Biol. Chem.  2008,  283, 11700-11713.
• "A Dicyanotriterpenoid Induces Cytoprotective Enzymes and Reduces Multiplicity of Skin Tumors in UV-Irradiated Mice"; Dinkova-Kostova, A.T.; Jenkins, S.N.; Wehage, S.L.; Huso, D.L.; Benedict, A.L.; Stephenson, K.K.; Fahey, J.W.; Liu, H.; Liby, K.T.; Honda, T.; Gribble, G.W.; Sporn, M.B.; Talalay, P. Biochem. Biophys. Res. Commun. 2008, 367, 859-865.
• "Efficient Reductive Acylation of 3-Nitroindoles"; Roy, S.; Roy, S.; Gribble, G.W. Tetrahedron Lett. 2008, 49, 1531-1533.
• "One-Pot Synthesis of Pyrrolylamides and Pyrrolylimides by Tin- and Indium-Mediated Reductive Acylation of 2- and 3-Nitropyrroles"; Fu, L.; Gribble, G.W. Synthesis 2008, 788-794.
• "Structure and Biosynthesis of Halogenated Alkaloids"; Gribble, G.W., In Modern Alkaloids – Structure, Isolation, Synthesis and Biology; Fattorusso, E; Taglialatela-Scafati, O., Eds.; Wiley-VCH: Weinheim, Germany, 2008, 591-618.
• "Isolation and Structure Determination of the Cembranoid Eunicin from a New Genus of Octocoral, Pseudoplexaura"; Sponholtz, III, W.R.; Bianco, M.A.; Gribble, G.W. Nat. Prod. Res. 2008, 22, 441-448.