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Leveraging Cyclopropanols in Natural Product Synthesis

在天然产物合成中利用环丙醇

基本信息

批准号：
2203224
负责人：
Jin Cha
金额：
$ 51.75万
依托单位：
Wayne State University
依托单位国家：
美国
项目类别：
Standard Grant
财政年份：
2022
资助国家：
美国
起止时间：
2022-04-01 至 2025-03-31
项目状态：
未结题

来源：
https://www.nsf.gov/awardsearch/showAward?AWD_ID=2203224&HistoricalAwards=false
关键词：
Leveraging Cyclopropanols Natural Product Synthesis

项目摘要

With the support of the Chemical Synthesis program of the Division of Chemistry, Professor Jin Cha of Wayne State University is developing efficient routes to important molecules which are utilized in organic or medicinal chemistry. Starting with readily available three-membered ring compounds, the research plan builds complex molecules in a modular approach to construct naturally occurring molecules endowed with desirable properties. The proposed work builds on a key modification in the initial three-membered ring formation to pave the way for new chemical syntheses. These studies will have potential for broader societal benefits, as convergent, environmentally benign and sustainable syntheses offer enabling tools in pharmaceutical, chemical, agricultural industry, and materials science. This project will provide excellent training for coworkers, from undergraduate research participants to post-doctoral fellows, including those from groups historically underrepresented in STEM (science, technology, engineering and mathematics) fields.With the support of the Chemical Synthesis program of the Division of Chemistry, Professor Cha of Wayne State University is studying an efficient synthesis of natural products with particular emphasis on efficiency and selectivity. Coupling (union) of two polyfunctional fragments lends itself to practical syntheses of complex molecules. The proposed study will focus on the development and application of cross-coupling reactions of cyclopropanols or the related titanacyclopropanes to develop concise synthetic routes. The Cha group will continue to utilize cyclopropanols as a unique family of nonracemic and attractively functionalized homologous enol equivalents in the C–C bond formation. Transition metal-catalyzed cross-coupling reactions of two segments include C-acylation, SN2’ alkylation, alkenylation, and alkynylation of cyclopropanols. The preparative power of the key synthetic methods are to be highlighted in projected concise total syntheses of an array of structurally novel and biologically important natural products. Among these targets are included gephyrotoxin, alkaloid 261C, scholarisine A, artemisinin, and mitomycin C.This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.

在化学系化学合成计划的支持下，韦恩州立大学的金查教授正在开发用于有机或药物化学的重要分子的有效途径。该研究计划从容易获得的三元环化合物开始，以模块化的方法构建复杂分子，以构建具有理想性质的自然产生的分子。拟议的工作建立在最初三元环形成的关键修改的基础上，为新的化学合成铺平了道路。这些研究将有可能带来更广泛的社会效益，因为融合的、环境友好的和可持续的合成在制药、化工、农业和材料科学中提供了有利的工具。这个项目将为同事提供极好的培训，从本科生研究参与者到博士后研究员，包括那些来自STEM(科学、技术、工程和数学)领域历史上代表性不足的群体。在化学系化学合成计划的支持下，韦恩州立大学的查教授正在研究一种高效的天然产物合成，特别强调效率和选择性。两个多官能团片段的偶联(结合)有助于复杂分子的实际合成。拟议的研究将侧重于环丙醇或相关的钛环丙烷的交叉偶联反应的开发和应用，以开发简洁的合成路线。CHA基团将继续利用环丙醇作为C-C键形成中独特的非外消旋和有吸引力的同系烯醇类等价物。过渡金属催化的两段交叉偶联反应包括环丙醇的C-酰化反应、SN2‘烷基化反应、烯基化反应和炔化反应。主要合成方法的制备能力将在一系列结构新颖和具有生物重要性的天然产物的预测简明全合成中得到突出。在这些目标中，包括地卟啉毒素、生物碱261C、苦参碱A、青蒿素和丝裂霉素C。这一奖项反映了NSF的法定使命，并通过使用基金会的智力优势和更广泛的影响审查标准进行评估，被认为值得支持。