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Sequential Coupling/Pericyclic Reactions of a Dihalogenated Pyrone for Complex Molecule Synthesis

用于复杂分子合成的二卤代吡喃酮的连续偶联/周环反应

基本信息

批准号：
1856228
负责人：
Richmond Sarpong
金额：
$ 48.5万
依托单位：
University of California-Berkeley
依托单位国家：
美国
项目类别：
Standard Grant
财政年份：
2019
资助国家：
美国
起止时间：
2019-06-01 至 2024-05-31
项目状态：
已结题

来源：
https://www.nsf.gov/awardsearch/showAward?AWD_ID=1856228&HistoricalAwards=false
关键词：
Sequential Coupling Pericyclic Reactions Dihalogenated

项目摘要

With this Award, the Chemical Synthesis Program of the NSF Division of Chemistry is supporting the research of Professor Richmond Sarpong of the University of California, Berkeley who is pursuing specific (selective) ways to modify molecules known as pyrones. The modifications produce new compounds that have important chemical properties. The research group is particularly interested in the synthesis of complex molecules found in small quantities in nature (natural products). The modification of pryones is conducted using metal catalysts but when there are multiple choices for modification, achieving a single, preferred option is challenging. Through the careful choice of chemical reagents and conditions, Professor Sarpong and coworkers strategically design specific changes in the starting molecules, setting the stage for the synthesis of compounds of potential pharmaceutical relevance. Professor Sarpong and his coworkers serve as mentors to under-represented minority students in the greater Oakland, CA area. They also visit classrooms and conduct demonstrations at area science festivals. Professor Sarpong continues to inspire students worldwide through TED-style talks.Professor Sarpong and his coworkers use 3,5-dibromo-2-pyrone for the synthesis of various classes of natural products. Key to this approach is site-selective cross-couplings to a dihalogenated pyrone, which sets the stage for sequential pericyclic processes resulting in a rapid increase in target-relevant complexity. Through this combination of controlled peripheral functionalization and rearrangements of the core structure (framework reconstruction), the synthesis of complex natural products such as secondary metabolites isolated from Incarvillea delavayi, Cephalotaxus sinensis and decahydroazulenes is studied. These advances provide complementary approaches to complex molecules of biological relevance starting from a relatively simple starting input, 3,5-dibromo-pyrone. As a part of this project, Professor Sarpong is training his coworkers and preparing them for careers in chemical industries.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.

有了这个奖项，NSF化学部的化学合成计划正在支持加州大学伯克利分校的里士满萨蓬教授的研究，他正在寻求特定的（选择性的）方法来修饰被称为吡喃酮的分子。这些修饰产生了具有重要化学性质的新化合物。该研究小组特别感兴趣的是在自然界中少量发现的复杂分子（天然产物）的合成。使用金属催化剂进行蛋白质的改性，但是当存在多种改性选择时，实现单一的优选选择是具有挑战性的。通过仔细选择化学试剂和条件，Sarpong教授及其同事战略性地设计了起始分子的特定变化，为合成具有潜在药物相关性的化合物奠定了基础。教授Sarpong和他的同事担任导师，以代表性不足的少数民族学生在大奥克兰，加利福尼亚州地区。他们还参观教室，并在地区科学节上进行示范。Sarpong教授继续通过TED风格的演讲激励世界各地的学生。Sarpong教授和他的同事使用3，5-二溴-2-吡喃酮合成各种天然产物。这种方法的关键是位点选择性交叉偶联到二卤代吡喃酮，这为连续的周环过程奠定了基础，从而导致目标相关复杂性的快速增加。通过这种控制外围功能化和核心结构重排（框架重建）的组合，研究了复杂天然产物的合成，如从角蒿属delavayi，红豆杉和decahydroazulenes分离的次级代谢产物。这些进展为从相对简单的起始输入3，5-二溴-吡喃酮开始的生物相关的复杂分子提供了补充方法。作为该项目的一部分，Sarpong教授正在培训他的同事，并为他们在化学工业中的职业生涯做准备。该奖项反映了NSF的法定使命，并通过使用基金会的知识价值和更广泛的影响审查标准进行评估，被认为值得支持。