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

在这个由化学部化学合成项目资助的项目中，哈维马德学院化学系的David Vosburg教授将采用仿生和生物友好的策略来合成抗生素、抗炎和抗结核的天然产物以及非天然衍生物。将开发有效和灵活的路线，这将导致这些生物活性化合物的首次合成制剂。最近开发的形成C-C和C=C键的方法在这项工作中占有突出地位，微波促进的交叉偶联反应也是如此。整体策略的核心是使用立体选择性，催化交叉偶联反应直接触发仿生多烯环化级联。还将进行理论研究，以确定和测量具有多种可能结果的级联中控制选择性的因素。更广泛的影响包括培训本科生，通过将社区学院和高中研究人员纳入该项目，扩大参与范围，与圣安东尼奥山学院和向上Bound建立HMC合作伙伴关系，并为新的绿色化学的发展做出贡献。这项工作将导致使用新开发的方法创新合成药物有用化合物的途径，可能发现新的生物活性分子，并更深入地了解仿生环化。成功的研究结果应该对生物学、有机合成、理论化学以及制药和化学工业等各个领域产生影响。该项目将尽可能展示绿色化学原理，并将为哈维穆德学院、圣安东尼奥山学院和当地高中的学生提供宝贵的培训经验，包括那些历史上在科学领域代表性不足的群体。

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.