Dearomatization Reactions in Synthesis

通过该奖项，美国国家科学基金会化学部门的化学合成计划支持俄勒冈州立大学教授Christopher M.Beaudry的研究，他正在研究用于制备药品、精细化学品和化学工业的积木分子的新化学反应。芳香环是许多精细化学品的共同特征。传统上，芳环被认为是稳定的、活性较低的化学实体；然而，Beaudry团队正在开发新的反应，以利用它们未被充分利用的反应性。它们将使临床药物如高三尖杉酯碱(用于白血病)、麦角美林(用于产后出血)和新型先导化合物如希莫林(在心血管研究中的潜在应用)的合成更加有效。这项研究的教育效益包括培养化学行业的博士生和本科生。此外，俄勒冈州学校的推广活动涉及科瓦利斯公立学校系统。博德里教授和他的研究团队开发了芳香环的新周环反应，将这些分子转化为新的增值分子。具体地说，它们通过控制取代将苯、吡喃、吡啶和相关的起始物质转化为其他环状和多环状产物。这项研究利用芳烃原料中连续的不饱和碳，得到了稠密的功能化产品。一个关键的方面是认识到极化的环加成偶联伙伴在这些键结构中提供了更高的反应性和区域选择性。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、2，3-二取代苯酚和含氮双环体系的制备。这项工作的更广泛影响包括培训化学家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提供良好的准备。这项研究可能会获得更长期的好处，因为高附加值目标的步骤省时、聚合合成的开发可以导致这些目标的更有效的制造过程。此外，博得利集团积极致力于接触未被充分代表的少数群体和第一代大学生，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。

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.