Asymmetric Synthesis of the Anticancer Agent (+)-Elacomine

Ryan Majinski, “Asymmetric Synthesis of the Anticancer Agent (+)-Elacomine”
Mentor: M Mahmun Hossain, Chemistry & Biochemistry

(+)-Elacomine is a natural anticancer agent found in certain shrubs of the Elaeagnus genus. It has been found to be toxic to melanoma cells while also having almost no effect on normal human cell lines. This allows for a uniquely targeted treatment to melanoma, and therefore elacomine has been the subject of recent synthetic research. Modeled after a recent synthetic route for (-)-coerulescine, a structurally similar analgesic agent, we devised an efficient method of creating elacomine in only six successive reactions. The first step consists of the formation of a 3-hydroxyacrylic acid ester, which has already been optimized. The second step involves the asymmetric alkylation of the acrylate product, and it is currently being optimized. After optimization of all steps using model compounds, we can apply these reaction parameters to the synthesis of the anticancer agent elacomine.

Comments

  1. Hello, and thank you for tuning in to my poster! This is my fourth and final year performing organic chemistry research in Dr. M Mahmun Hossain’s Laboratory Group. The two main projects I worked on during my time here were a Detailed Study of Acid-Catalyzed Reactions of Carbonyl Compounds with Ethyl Diazoacetate, and this current project, presented above. I am graduating this month with a degree in Biomedical Science, and I have accepted a full time position as a Medical Laboratory Scientist at Children’s Wisconsin. I have greatly enjoyed my time both at UWM and in Dr. Hossain’s laboratory, and I would also like to thank the whole Office of Undergraduate Research for their continued support for my research projects.

    If you have any questions or suggestions, please post them below, and I will try to answer them as best I can!

    -Ryan

  2. You did a wonderful job on this research project. You were very informative. Your poster looks great.

Leave a Reply

Your email address will not be published.