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

美国国家科学基金会化学部化学合成计划支持伊利诺伊州立大学化学系安迪·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。这些新反应在有机化学中很重要，因为它们能够有效和选择性地将简单分子转化为更复杂的三维分子。许多生物活性分子和药物具有类似于这些反应构建的三维结构。更广泛地说，有机化学的发展促进了生物、医学和材料领域的发展，并促进了经济发展和环境可持续发展。本科生的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。通过实践指导和接触最先进的仪器设备，米切尔教授为本科生继续在优秀的研究生院课程中接受培训或进入劳动力大军成为生产性化学家做好准备。米切尔团队追求的是具有持久和广泛影响的潜在综合挑战，但目标可控，适合新手研究人员。此外，米切尔教授还与伊利诺伊州夏季研究院合作，指导高中生，这些学生通常来自代表人数较少的群体。这种为期一周的密集研究经验可以提供必要的火花，让这些年轻的学生用有机合成的奇观来激发他们。这项研究的主要目的是扩大环加成反应可获得的化学空间，以构建新颖的、否则无法获得的杂环支架。具体地说，米切尔小组正在研究各种基于氧化吡喃的[5+2]过程的范围和反应途径。利用Feist-Bénary呋喃合成，他们正在致力于合成毒素十二烷A，并开发一种非对映选择性的[5+2]三碳组分。在一个新的方向上，他们正在建立对氧化吡喃中间体的激活参数。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。该教育计划包括向当地高中宣传，向学生介绍有机合成的历史和现实意义。高中生通过伊利诺伊州夏季研究院在研究实验室接受指导。这些外展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.