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Wednesday, April 26 • 10:30am - 10:50am
Natural Dibenz[B,F]Oxepin As A Potential Novel Antibacterial Agent: Progress Towards The Synthesis And Optimization Of Empetroxepin A And B

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The increase in multi-drug resistant strains of pathogenic bacteria has made the issue of bacterial resistance a global health concern. New classes of antibacterial drug compounds, able to work outside existing mechanisms of resistance, are needed to combat these infections. Natural product-based drug discovery is an effective method in the development of new classes of antibiotics due to the chemically unique structures characteristic of naturally occurring compounds. This study aims to develop a viable antibacterial drug using Empetroxepin A and B, novel dibenz[b,f]oxepin natural products, as the lead compounds. The natural products will be synthesized in seven steps from commercially available 3,4,5-trimethoxytoluene. To date, the first five steps have been completed successfully through a Wittig olefination of trimethylsilane-protected salicyladlehyde with the phosphonium salt generated from the toluene starting material. The desired phosphonium salt was synthesized through aromatic bromination and radical benzylic bromination of the starting material. High yields (68-99%) have been achieved on large scales for each of these steps. Hydrogenation of the alkene bridge formed by the Wittig olefination has also been completed though only low yields have been obtained to date. The remaining two steps in the total synthesis include a copper oxide catalyzed etherification ring closure followed by selective deprotection to give both Empetroxepin A and B. Once synthesis of the lead compounds has been completed, the synthetic route will be used to develop analogs for structure activity relationship studies to optimize the natural product’s antibacterial activity.


Wednesday April 26, 2017 10:30am - 10:50am PDT
014 Zeis Hall