College Honors Program

Synthetic Studies of Cyclocurcumin

Date of Creation

5-17-2024

Document Type

Campus Access Only

Department

Chemistry

First Advisor

Kevin Quinn

Abstract

Turmeric, a staple in traditional Indian cuisine, not only gives curry its distinct color and taste but also holds significance in traditional medicine. It is composed of many biologically active molecules, with cyclocurcumin, classified as a non-curcuminoid, being the primary focus of this study. This molecule has shown anticancer, antivasoconstrictive and immune-modulating biological activity, making it a target for natural product synthesis. While its medicinal potential is important, our goal is to use cyclocurcumin as a platform for the development of a regioselective carbon-carbon oxidation reaction. This paper explores three different approaches to synthesizing cyclocurcumin through the use of a model system. The Prins cyclization and aldol addition approach will enable us to assess whether the oxidation reaction can differentiate between two oxidation sites with subtle differences. Preliminary findings indicate the potential viability of the aldol addition approach that, if successful, will allow us to study the oxidation reaction. The Diels-Alder approach also holds promise but does not provide an avenue for examining the reaction of interest. All three approaches employ coupling reactions that are easily amenable to the synthesis of not only cyclocurcumin but any of its analogs if successful.

Comments

Reader: Bianca Sculimbrene

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