Dearomatization Reactions in 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俄勒冈州立大学的Christopher M. Beaudry教授的研究，他正在研究用于制备药物、精细化学品和化学工业的基本分子的新化学反应。芳香环是许多精细化学品的共同特征。传统上，芳香环被认为是稳定的，反应性较低的化学实体；然而，Beaudry小组正在开发新的反应来利用它们未被充分利用的反应性。它们将能够更有效地合成临床药物，如homharkingtonine（治疗白血病），ergometrine（治疗产后出血），以及新的先导化合物，如himgaline（潜在应用于心血管研究）。这项研究的教育效益包括培养博士研究生和本科生从事化学工业。此外，俄勒冈州学校的外展活动涉及科瓦利斯公立学校系统。Beaudry教授和他的研究小组开发了新的芳香环周环反应，将这些分子转化为新的增值分子。具体来说，它们将苯、吡酮、吡啶和相关原料转化为其他环和多环产物，并控制取代。该研究利用芳烃原料的连续不饱和碳来获得密集的功能化产物。一个关键的方面是认识到，极化环加成耦合伙伴提供增加的反应性和区域选择性在这些键的结构。这项工作解决了化学合成中长期存在的问题，如4-取代吲哚、2,3-二取代酚和含氮双环体系的制备。这项工作的广泛影响包括培训化学家在复杂有机合成的实践和策略；为他们在农化、制药和精细化工行业的职业生涯做好准备。这项研究的长期效益可能会随着节步的发展而获得，高附加值目标的聚合合成可以导致更有效的制造这些目标的过程。此外，Beaudry集团积极参与接触代表性不足的少数民族和第一代大学生，并为他们提供接触合成化学现代研究的机会。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 Christopher M. Beaudry of Oregon State University who is investigating new chemical reactions that are used to prepare pharmaceuticals, fine chemicals, and building-block molecules for the chemical industry. Aromatic rings are common features of many fine chemicals. Traditionally, aromatic rings are viewed as stable, less reactive chemical entities; however, the Beaudry group is developing new reactions to harness their underutilized reactivity. They will enable more efficient syntheses of clinical pharmaceuticals such as homoharringtonine (for leukemia), ergometrine (for postpartum bleeding), and novel lead compounds such as himgaline (potential applications in cardiovascular research). Educational benefits of this research include training PhD students and undergraduates for careers in the chemical industry. Additionally, outreach activities in Oregon schools involve the Corvallis public school system.Professor Beaudry and his research team develop new pericyclic reactions of aromatic rings that transform these molecules into new value-added molecules. Specifically, they are transforming benzenes, pyrones, pyridines, and related starting materials into other cyclic and polycyclic products with control over substitution. The research leverages the contiguous unsaturated carbons of the arene starting materials to give densely functionalized products. A key aspect is the recognition that polarized cycloaddition coupling partners offer increased reactivity and regioselectivity in these bond constructions. This work solves long-standing problems in chemical synthesis, such as the preparation of 4-substituted indoles, 2,3-disubstituted phenols, and nitrogen-containing bicyclic systems. Broader impacts of the work include training chemists in the practice and strategy of sophisticated organic synthesis; preparation that serves them well for careers in the agrochemical, pharmaceutical, and fine chemical industries. Longer term benefits of this research may obtain as the development of step-saving, convergent syntheses of high value-added targets could lead to more efficient processes for the manufacture of these targets. Moreover, the Beaudry group is actively engaged in reaching under-represented minorities and first-generation college students and in providing them with exposure to modern research in synthetic chemistry.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.