George O'Doherty

Full Professor

117 Hurtig Hall
Tel: 617.373.4817
Fax: 617.373.8795
g.odoherty@neu.edu
O'Doherty Group Laboratory

Organic, Bioorganic & Medicinal Chemistry

Education:

1993 Ph.D. The Ohio State University
1987 B.S. Rennselaer Polytechnic Institute

Research Interests

My research group has been working in two related areas of organic synthesis: carbohydrate synthesis and natural product synthesis. The unifying theme that connects our research in these two areas is our use of asymmetric catalysis and the desire to create new antitumor and antimicrobial compounds. Fundamental to our approach is the development of highly efficient routes that transform, via catalysis, inexpensive achiral starting materials into enantiopure products, which are poised for the conversion into complex molecules with biologically relevant properties (i.e. enantioselective synthesis of a new “chiral pool” via asymmetric catalysis). Some successful examples of this de novo approach to both natural product and carbohydrate targets are outlined below. The ultimate goal of these synthetic projects is to develop enantioselective routes to these complex molecules in sufficient quantities that are amenable for biomedical investigations.

Selected Publications

"Synthesis and Evaluation of the α-D-/α-L-Rhamnosyl and Amicetosyl Digitoxigenin Oligomers as Anti-tumor Agents" H.-Y. L. Wang, Y. Rojanasakul, and G. A. O'Doherty, Org. Lett. Pending.

"Synthesis of Several Cleistrioside and Cleistetroside Natural Products via a Divergent De Novo Asymmetric Approach" B. Wu, Li, M. and G. A. O'Doherty, Org. Lett. (2010), 12, 5466-9.

"De Novo Synthesis of Glycosylated Methymycin Analogues" S. A. Borisova, S. R. Guppi, H. J. Kim, B. Wu, H.-w. Liu and G. A. O'Doherty, Org. Lett. (2010), 12, 5150-5153.

"Stereochemical Survey of Digitoxin Monosaccharides:" H.-Y. L. Wang, W. Xin, M. Zhou, T. A. Stueckle, Y. Rojanasakul, and G. A. O'Doherty, ACS Med. Chem. Lett. Pending.

"Total Synthesis of Jadomycin A and Carbasugar Analogue of Jadomycin B" M. Shan, E. U. Sharif and G. A. O'Doherty, Angew. Chem. Int. Ed. (2010), 49, 9492-9495.

"De Novo Asymmetric Synthesis of the D-/L-Disaccharide Portion of Sch 47555" X. Yu, M. Li and G. A. O'Doherty, Heterocycles, Pending. Special issue in honor of Prof. Albert Eschenmoser's 80th B'day.

"A General Approach to Anionic Acid-Labile Surfactants with Tunable Properties" M. Li, M. Powell, T. Razunguzwa and G. A. O'Doherty, J. Org. Chem. (2010), 75, 6149-6153.

"Total Synthesis of Fostriecin: Via a Regio- and Stereoselective Polyene Hydration, Oxidation and Hydroboration Sequence" D. Gao and G. A. O'Doherty, Org. Lett. (2010), 12, 3752-3755.

"Synthesis of SL0101 Carbasugar Analogues: Carbasugars via Pd-Catalyzed Cyclitolization and Post Cyclitolization Transformations" M. Shan, and G. A. O'Doherty, Org. Lett. (2010), 12, 2986-2989.

"A Direct Comparison of the Anticancer Activities of Digitoxin MeON-Neoglycosides and O-Glycosides: Oligosaccharide Chain Length-Dependant Induction of Caspase-9-Mediated Apoptosis" A. Iyer, M. Zhou, N. Azad, H. Elbaz, L. Wang, D. K. Rogalsky, Y. Rojanasakul, G. A. O'Doherty and J. M. Langenhan, ACS Med. Chem. Lett. (2010), 1, 326-330.