Reaction Kinetics of Diels-Alder Reactions Useful in Pharmaceutical Synthesis
Chemistry, Dr. Bur
About My Research (2009):
The Diels-Alder reaction is an important reaction in Organic Chemistry. It can be used to form molecules that have two rings. These bicyclic ring structures are found in many natural products that are used in drug research. My project is focusing on how fast the Diels-Alder reaction is happening between two molecules. I am tracking the speed of the two reacting molecules to see how long they take to form a product. I am also changing the sizes of the two reacting molecules to see if larger molecules react slower to form a product and if smaller molecules react faster to form a product. By knowing the speed of the reaction we can better understand how fast the bicyclic ring structures are formed and know more about the rate at which drugs can be made.
This research was funded by the American Chemical Society Petroleum Research Fund.
The Diels-Alder reaction is a well known mechanism in Organic Chemistry. The intramolecular reaction between a diene and a dienophile can form a bicyclic ring structure that is commonly found in natural products, which often have biological activity. We are focusing on the rate at which the Diels-Alder reaction occurs between a variety of maleate derivatives and silyloxy furan derivatives. By tracking the rate of the reaction of the less sterically hindered reactants, dimethyl maleate with trimethylsiloxyfuran, and the more sterically hindered reactants, diethyl maleate with triethylsiloxyfuran, we can quantitatively understand the Diels-Alder mechanism. These kinetic studies will inform us more about the Diels-Alder intermediate and help us better characterize the mechanism so that we have an enhanced understanding of how the natural occurring, bicyclic compounds are synthesized.
In the student's own words:
I have found that research at Gustavus is more personally focused because you get to work on your own project with the individualized help from your research advisor. I have found that I have been forced to problem solve and independently inform myself on my personal project. Because of this I feel like I have become an expert on my topic and really succeeded in the research setting.
My 2007 Summer Research Project:
Organic Synthesis of Pyrrolizidine Alkaloids
This project focuses on the synthesis of a bicyclical pyrrolizidine alkaloid derived from an amine and a carboxylic acid. The amine was synthesized from methionine by a series of reactions. The carboxylic acid was synthesized from methyl acrylate and nitromethane. The amine and the carboxylic acid were coupled with DCC and D-MAP to form an intermediary amide. We are currently working on the formation of the bicyclical alkaloid using a lewis acid as a catalyst.
More thoughts about research:
My summer research project included both Organic Synthesis and kinetic studies. I found that these scientific studies were a collaboration of several chemistry classes I have taken at Gustavus. For the first time I was able to use knowledge I have acquired from Physical Chemistry, Organic Chemistry and Analytical Chemistry and see how they all are connected in a research setting.
- Nina came back to the Bur lab in 2009
- Nina presented the results of her 2007 research at the 2007 Chemistry-Biology Fall Research Symposium.