RUI: Synthesis of Highly Functionalized Heterocyclic Scaffolds

RUI：高功能化杂环支架的合成

• 批准号: 1665139
• 负责人: Carolyn Anderson
• 金额: $ 29.97万
• 依托单位: Calvin University
• 依托单位国家: 美国
• 项目类别: Continuing Grant
• 财政年份: 2017
• 资助国家: 美国
• 起止时间: 2017-05-01 至 2022-04-30
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=1665139&HistoricalAwards=false
• 关键词: RUI; Synthesis; Highly; Functionalized; Heterocyclic

In this RUI project funded by the Chemical Synthesis Program, Professor Carolyn Anderson of the Department of Chemistry and Biochemistry at Calvin College creates new methods for the synthesis of complex organic heterocycles. These are substances which contain nitrogen in a ring. New synthetic routes are primarily based on reactions catalyzed by gold (III). Challenging synthetic targets include indolizine and isoquinoline alkaloids, heterocyclic compounds which possess potential medicinal properties. In addition, this award supports 8-10 week summer visitations to Calvin College by senior graduate students from major research institutions. These visitations provide training for future careers as a PUI faculty member.This research expands the suite of chiral and achiral methods for preparing highly functionalized trisubstituted indolizine and N-alkyl 2-pyridone structures. This new chemistry makes these species, and their analogues, available to the broader chemical community. Basic knowledge related to mechanistic and asymmetric gold(III) catalysis is an important product of this research. Successful development of these methodologies and targets impacts the synthetic community as well as those involved in the development of organic materials, medicinal leads, and asymmetric transformations. This research provides hands-on laboratory training for undergraduate research collaborators and pre-college students, especially those from historically underrepresented groups. In addition, this award enables senior graduate students, who intend to pursue academic careers at primarily undergraduate institutions, to spend time during a summer as a member of the PI's laboratory. In this role, the visiting graduate students gain essential experience in running a productive undergraduate research group, while being mentored directly by the PI.

在这个由化学合成计划资助的RUI项目中，卡尔文学院化学与生物化学系的Carolyn安德森教授创造了合成复杂有机杂环的新方法。 这些是在环中含有氮的物质。新的合成路线主要基于金（III）催化的反应。其中，中氮茚和异喹啉类生物碱是一类具有潜在药用价值的杂环化合物。此外，该奖项支持8-10周的夏季访问卡尔文学院的高级研究生从主要的研究机构。这些访问提供了培训，为未来的职业生涯作为一个PUI的教员。这项研究扩展了一套手性和非手性的方法，用于制备高度官能化的三取代中氮茚和N-烷基2-吡啶酮结构。这种新的化学物质使这些物种及其类似物可用于更广泛的化学界。与机械和不对称金（III）催化相关的基础知识是这项研究的重要成果。这些方法和目标的成功开发影响了合成社区以及那些参与有机材料，药用铅和不对称转化的发展。这项研究为本科研究合作者和大学预科学生提供了动手实验室培训，特别是那些来自历史上代表性不足的群体。此外，该奖项使高年级研究生，谁打算在主要本科院校追求学术生涯，花时间在夏季作为PI的实验室的成员。在这个角色中，访问研究生获得了运行一个富有成效的本科生研究小组的基本经验，同时直接由PI指导。

项目成果

Synthesis of Ester-Substituted Indolizines from 2-Propargyloxypyridines and 1,3-Dicarbonyls

由2-炔丙氧基吡啶和1,3-二羰基化合物合成酯取代的中氮茚

• DOI: 10.1021/acs.joc.2c01219
• 发表时间: 2022
• 期刊: The Journal of Organic Chemistry
• 作者: Anderson, Carolyn E.;Bos, Haleigh I.;Dreher, Daniel M.;Hartgerink, Colin T.;Scholtens, Chase J.;Staples, Richard J.
• 通讯作者: Staples, Richard J.