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.