RUI: Exploration of [5+2] Cycloadditions toward Novel Heterocyclic Scaffolds

美国国家科学基金会化学部的化学合成计划支持伊利诺伊州州立大学化学系的安迪·米切尔教授的项目。 米切尔教授和他的学生正在开发新的化学反应，形成由原子环组成的分子。这些新的反应在有机化学中很重要，因为它们使简单分子能够有效和选择性地转化为更复杂的三维分子。许多生物活性分子和药物具有与这些反应所构建的结构类似的三维结构。更一般地说，有机化学的发展推动了生物学，医学和材料领域的发展，并促进了经济发展和环境可持续性。本科生科研训练在学生成长为科学家的过程中起着不可或缺的作用。 通过亲自指导和接触最先进的仪器，米切尔教授为本科生做好准备，让他们继续在优秀的研究生院项目中接受培训，或作为高效化学家进入劳动力市场。Mitchell小组追求具有持久和广泛影响潜力的综合挑战，但具有适合新手研究人员的可管理目标。此外，米切尔教授与伊利诺伊州夏季研究学院的合作伙伴，指导高中生，往往从代表性不足的群体。这种密集的为期一周的研究经验可以提供必要的火花，激发这些年轻的学生与有机合成的奇迹。该研究的主要目的是扩大环加成反应的化学空间，以构建新的和其他方式无法获得的杂环支架。具体来说，米切尔小组正在研究各种基于氧化吡喃[5+2]过程的范围和反应途径。利用Feist-Bénary呋喃合成法，他们正致力于合成toxicodenane A并开发非对映选择性[5+2]三碳组分。在一个新的方向，他们正在建立对oxidopyrylium中间体的活化参数。他们利用这些信息来开发解决当前选择性限制的反应。作为更广泛影响的一部分，下一代科学家接受培训，在生物相关分子的背景下提出重要问题。教育计划包括与当地高中的联系，向学生介绍有机合成的历史和当前意义。高中生通过伊利诺伊州夏季研究学院在研究实验室接受指导。这些推广活动与研究计划很好地结合在一起。

The Chemical Synthesis Program of the NSF Chemistry Division supports the project by Professor Andy Mitchell in the Department of Chemistry at Illinois State University. Professor Mitchell and his students are developing new chemical reactions that form molecules comprised of rings of atoms. These new reactions are important in organic chemistry because they enable efficient and selective transformation of simple molecules to three-dimensional molecules of greater complexity. Many biologically active molecules and pharmaceuticals have three-dimensional structures similar to those constructed by these reactions. More generally, developments in organic chemistry advance the fields of biology, medicine, and materials, as well as promoting economic development and environmental sustainability. Undergraduate student research training performs an indispensable role in the growth of students into scientists. Through hands-on mentorship and exposure to state-of-the-art instrumentation, Professor Mitchell prepares undergraduates to continue their training at excellent graduate school programs or to enter the workforce as productive chemists. The Mitchell group pursues synthetic challenges with potential for enduring and broad impact, yet with manageable goals suitable for novice researchers. In addition, Professor Mitchell partners with the Illinois Summer Research Academy to mentor high school students, often from underrepresented groups. This intensive one-week research experience can provide the spark necessary to excite these young students with the wonders of organic synthesis. The main objective of the proposed research is to expand the chemical space that is accessible by cycloaddition reactions in order to construct novel and otherwise inaccessible heterocyclic scaffolds. Specifically, the Mitchell group is investigating the scope and reaction pathway of various oxidopyrylium-based [5+2] processes. Utilizing the Feist-Bénary furan synthesis, they are working toward the synthesis of toxicodenane A and developing a diastereoselective [5+2] three-carbon component. In a new direction, they are establishing activation parameters toward oxidopyrylium intermediates. They use this information to develop reactions that address current selectivity limitations. As part of broader impacts, next generation scientists are trained to ask important questions in the context of biologically relevant molecules. The educational plan includes outreach to local high schools to introduce students to the historical and current significance of organic synthesis. High school students are mentored in a research lab through the Illinois Summer Research Academy. These outreach activities are well integrated with the research program.