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Wednesday, April 22 • 2:30pm - 4:30pm
Synthesis and Modification of Spiromastixone I and the Spriomastixone Central Ring

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Depsidones are tricyclic natural products with a wide range of known antibacterial properties. The Spiromastix sp. fungus was recently found in the deep sea near Japan and has been found to produce 15 new depsidone molecules known collectively as Spiromastixones A-O. The main goals of this research are to first successfully synthesize the backbone of depsidone molecules and then to experiment with modifications to the central ring and its substituents. The first reaction of the backbone synthesis, which involved the addition of catechol, benzyl bromide, and potassium carbonate in acetonitrile, produced the desired benzyl protected catechol in 19% yield. The success of this reaction was confirmed by 1H-NMR data. This product was then esterified with 2-bromobenzoic acid in 0.1M acetic anhydride under reflux conditions. Experiments have been completed on a combination of the first two reactions to increase product yields, and 1H-NMR data is currently being collected for confirmation. Later experiments include the total synthesis of Spiromastixone I and investigation of the modification of the aromatic ring substituents.


Wednesday April 22, 2015 2:30pm - 4:30pm PDT
Wilma Sherrill Center Grimes Atrium