Matthew Donahue, Ph.D.

Assistant Professor, Department of Chemistry and Biochemistry

The Donahue group is seeking enthusiastic students interested in doing research on topics related to natural product total synthesis and reaction method development. Targets of interest include the bioactive Lycopodium alkaloids magellanine and palhinine A and new heterocyclic ureas and guanidines. Students will learn practical laboratory skills relating to organic and analytical chemistry while working on complex problems. They will be trained on how to set-up, analyze and purify organic reactions. Hands on training will be provided for department instrumentation including infrared spectroscopy (IR), high-pressure liquid chromatography-mass spectrometry (LC-MS), and nuclear magnetic resonance spectroscopy (NMR) for the characterization of new chemical entities. Over the course of the research they will develop scientific literacy by reading the primary chemical literature. As the research progresses students will be expected to present results at internal and external scientific meetings.

8. Donahue, M. G. “(E)-1-(Phenylseleno)-2-(trimethylsilyl)ethane.” Handbook of Reagents for Organic Synthesis: Reagents for
Silicon-Mediated Organic Synthesis, Fuchs, P. L., Ed. 2011, 39-42.

7. Cwynar, V. A.; Donahue, M. G.; Hart, D. J.; Mbogo, G.; Yang, D. “Two Approaches to Diverting the Course of a Free Radical Cyclization: Application of Cyclopropylcarbinyl Radical Fragmentations and Allenes as Radical Acceptors.” J. Org. Chem., 2009, 74 (22), 8726-8732.

6. Hong, K. B.; Donahue, M. G.; Johnston, J. N. “Comparison of Triazolinium Triflate Fragmentation Rates as a Tool to Assay Relative Competency of Brønsted Bases in N→N Proton Transfer.” Bioorg. Med. Chem. Lett. 2009, 19 (17), 4971-4973.

5. Hong, K. B.; Donahue, M. G.; Johnston, J. N. “On the Nature of Rate Acceleration in the Synthesis and Fragmentation of
Triazolines by Brønsted Acid: Secondary Catalysis by Water (Hydronium Triflate).” J. Am. Chem. Soc. 2008, 130, 2323-2328.

4. Donahue, M. G.; Johnston, J. N. “Preparation of a Protected Phosphoramidon Precursor via an H-Phosphonate Coupling Strategy.” Bioorg. Med. Chem. Lett. 2006, 16, 5602-5604.

3. Cwynar, V. A.; Donahue, M. G.; Hart, D. J.; Yang. D. “Quassinoid Support Studies: Fused Carbocycle Synthesis from Benzoic Acid
Derivatives via 5-Hexynyl and 6-Heptynyl Radical Cyclizations.” Org. Lett. 2006, 8(20), 4577-4580.

2. Donahue, M. G.; Hart, D. J. “C19-Quassinoid Model Studies: Preparation of trans-Perhydroindans via a Vinylogous Mukaiyama
Aldol-Free Radical Cyclization Route.” Can. J. Chem. 2004, 82(2), 314-317.

1. Kolb, V. M.; Donahue, M. G.; Putnam, E. A.; Meyers, C. Y.; Robinson, P. A. “Cyclopropyl m-Nitrophenyl Ketone.” Acta Cryst. 2002, E58, o1161-o1163.