Organic chemical synthesis holds an essential role in the creation of complex molecules with a variety of every day applications from pharmaceuticals to cosmetics. As such, our group is interested in a class of highly substituted cyclohexene compounds that behave as anti-fungal agents, and are used as fragrances and preservatives. The goal of this research is to develop innovative synthetic methods for these compounds using inexpensive and readily available materials. We have recently optimized a one-step synthesis for a material that shows promise as a potent anti-microbial agent. Our current project seeks to develop the synthesis of similar compounds utilizing Diels-Alder chemistry with α-β unsaturated ketones. However, synthesis of these products has proven to be challenging which may be due to added steric and electronic effects in the dienophiles, decreasing overall reactivity. As a result, a variety of Lewis acid catalysts and purification techniques have been investigated. Our developments will be discussed in detail.

Synthetic investigation of highly substituted cyclohexene compounds via Diels-Alder reactions

251st National Meeting (2016)

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