Asymmetric Synthesis of Complex Heterocycles from Simple Cyclopropanes

该项目旨在开发供体-受体环丙烷，作为一系列正式[3+2]环加成反应的简单但广泛有用的构建块。将研究用醛、烯酮、环亚胺、腈和偶氮化合物拦截路易斯酸活化的丙二醇环丙烷，分别产生四氢呋喃、环烯醇醚、双环吡咯烷、吡咯烷和吡唑烷。该项目可能会导致快速获取天然存在的生物活性化合物的关键亚结构，如克拉二萜。通过这个奖项，有机和大分子化学项目支持了北卡罗来纳大学教堂山分校化学系杰弗里·约翰逊教授的研究。约翰逊教授的研究工作广泛地涉及化学合成领域。在这项资助下发展的化学研究预计将对在实验室中制备结构有趣的杂环结构的效率产生积极影响。这种亚结构在具有生物活性的天然产物和药物制剂中普遍存在。

This project seeks to develop donor-acceptor cyclopropanes as simple, but broadly useful building blocks for a range of formal [3+2] cycloaddition reactions. Intercepting Lewis acid activated malonyl cyclopropanes with aldehydes, ketenes, cyclic imines, nitriles, and azo compounds will be studied to deliver tetrahydrofurans, cyclic enol ethers, bicyclic pyrrolidines, pyrrolines, and pyrazolidines, respectively. The project could lead to the rapid access to key substructures of naturally occurring biologically active compounds like the cladiellin diterpenes.With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Professor Jeffrey Johnson of the Department of Chemistry at the University of North Carolina at Chapel Hill. Professor Johnson's research efforts are broadly in the area of chemical synthesis. The chemistry to be developed under the aegis of this grant is projected to positively impact the efficiency with which structurally interesting heterocyclic structures may be prepared in the laboratory. Such substructures are ubiquitous in biologically active natural products and medicinal agents.