RUI: MIDA Boronates and Biomimetic Cascades for the Syntheses of Bioactive Beilschmiedia Metabolites

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In this project funded by the Chemical Synthesis Program of the Chemistry Division, Professor David Vosburg of the Department of Chemistry at Harvey Mudd College (HMC) will employ biomimetic and bio-friendly strategies for the syntheses of antibiotic, anti-inflammatory, and antitubercular natural products as well as unnatural derivatives. Efficient and flexible routes will be developed that should result in the first synthetic preparations of each of these bioactive compounds. Recently developed methods for forming C-C and C=C bonds feature prominently in this work, as do microwave-promoted cross-coupling reactions. Central to the overall strategy is the use of stereoselective, catalytic cross-coupling reactions to directly trigger biomimetic polyene cyclization cascades. Theoretical studies will also be carried out to determine and measure the factors that control selectivity in cascades that have multiple possible outcomes. The broader impacts include training undergraduate students, broadening participation through the inclusion of community college and high school researchers on the project, building HMC partnerships with Mount San Antonio College and Upward Bound, and contributing to the development of new green chemistry. This work will result in innovative synthetic routes to medicinally useful compounds using newly developed methodologies, the possible discovery of novel bioactive molecules, and deeper insight into biomimetic cyclizations. Successful results should have an impact on a variety of areas: biology, organic synthesis, theoretical chemistry, and the pharmaceutical and chemical industries. This project will showcase green chemical principles when possible and will provide valuable training experiences for students from Harvey Mudd College, Mount San Antonio College, and local high schools, including those from groups historically underrepresented in the sciences.