Final Post: Summer Reflection

Summer research was an experience that I will never forget. There were times when it was difficult or frustrating but all the things I learned were incredible and I am so thankful I was given this opportunity. Being able to work for nine weeks straight on my project gave me a much deeper understanding of my specific reactions as well as the background literature relating to my research. I was able to acquire positive results that will allow me to keep moving forward in the fall.

The goal for the summer was to verify the initial steps in my synthesis of the pyrrolodiketopiperazine and move closer to a known natural product. Both of these goals were achieved. By the end of the summer, I had my initial reactions in the sequence all with yields above 60% and a secondary aldol condensation with a yield of 93%. This gave me a strong foundation to build off of. The last three weeks that I worked were focused towards nannozinone B, which is a natural product with some anticancer properties. The reactions I was running were on small scales so the products could not be accurately analyzed since they were not purified. However, I have a new research plan that I will be using in fall to move towards a full synthesis.

The product of the second aldol condensation adds a benzaldehyde onto the core pyrrolodiketopiperazine and has been observed as a more stable compound. Therefore, I have based the research I will do in the fall starting with this compound. First, we plan to use a hydrogenation reaction so that the double bond will be opened. Then a grignard reaction will  be used to add a new group and the oxygen can be removed as water. Finally, an oxidation reaction will be used to product the product nannozinone B. I will begin testing this reaction sequence when the semester begins and hope to write a paper with Dr. Scheerer by the end of my senior year.

new reaction pathway

I am so thankful for the opportunities and experiences I had this summer. I learned a lot about not only working in a lab but conducting the background research in literature required to move forward. Thank you to the Charles Center for the grant that gave me this chance and I look forward to continuing my research soon.