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

美国国家科学基金会化学部的化学合成项目通过该奖项支持加州大学伯克利分校的Richmond Sarpong教授的研究，他正在寻找特定的（选择性的）方法来修饰被称为pyroones的分子。这些修饰产生了具有重要化学性质的新化合物。该研究小组对在自然界中少量发现的复杂分子（天然产物）的合成特别感兴趣。丙酮的改性是使用金属催化剂进行的，但当有多种改性选择时，实现单一的首选方案是具有挑战性的。通过仔细选择化学试剂和条件，Sarpong教授及其同事策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。教授萨蓬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，加州地区。他们还参观教室，并在地区科学节上进行示范。萨蓬教授继续通过ted式的演讲激励全世界的学生。Sarpong教授和他的同事使用3,5-二溴-2-吡咯酮来合成各种类型的天然产物。这种方法的关键是与二卤代吡啶酮的位点选择性交叉偶联，这为连续的周环过程奠定了基础，从而导致与靶标相关的复杂性迅速增加。通过控制外周功能化和核心结构重排（框架重建）相结合，研究了从Incarvillea delavayi， Cephalotaxus sinensis和decahydroazulene中分离的次生代谢物等复杂天然产物的合成。这些进展为从相对简单的起始输入3,5-二溴吡咯酮开始研究具有生物学意义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的职业生涯做好准备。该奖项反映了美国国家科学基金会的法定使命，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。

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.