Erin Realini - Fall 2014 Eagle SPUR Recipient

   Mentor:Matthew Donahue, PhD
Project:An Approach Towards the Lycopodium Alkaloid Magellanine Utilizing the Tsuji-Trost Variant of the Winstein-Masamune Spirocyclization

For over a year now, I have conducted research in the area of organic synthesis in the Department of Chemistry and Biochemistry. As a certified senior pharmacy technician working for Walgreens, I have always been curious how prescription drugs are developed. The research project I am working on in Dr. Matt Donahue’s lab has given me a better understanding of this process. The Donahue Research Group has ongoing projects in the synthesis of naturally occurring molecules produced from plants. These molecules often have unique biological activity that can be used for treatment of diseases. The anticancer agent Taxol, that is isolated from the Pacific Yew Tree, is a prime example of this. To provide patients with sufficient doses of these life-saving molecules, biomedical researchers must make large quantities of them in the lab. To do this effectively, the reactions that join the building blocks must be efficient. 


My project involves the synthesis of a substructure of the Lycopodium alkaloid magellanine. Alkaloids are molecules that contain nitrogen, along with carbon and hydrogen. The analgesic morphine is an example of an alkaloid that is important to pain management. The reaction that I have been developing involves creating a difficult carbon-carbon bond to make a carbon atom bonded to four other carbon atoms.  The reaction uses an existing carbon based ring precursor to append a second carbon based ring via cyclization resulting in a spirocycle. 


Over the course of this research, I have presented my results at two American Chemical Society meetings, one in Nashville, TN and most recently at the National Organic Symposium in Baltimore, Maryland. The Eagle SPUR Award I received from the Center for Undergraduate Research supported my travel to present in Baltimore. It was exciting to present a poster to hundreds of students and experts in the field of organic chemistry. The experience made all the ups and downs of research worth it! As a senior biochemistry major, I encourage every undergraduate to do research. It makes you see the big picture of everything you learn in lectures. For example, I have used high performance liquid chromatography and nuclear magnetic resonance instruments on a regular basis and can now interpret my own data. This skill will be useful to me as I apply to graduate school in medicinal chemistry in the near future. SMTT!