Synthesis Driven by Release of Ring Strain

在这个由化学系化学合成项目资助的项目中，韦恩州立大学化学系的查教授正在研究几种在有机和药物化学中具有实用性的分子结构单元的有效制备。 该研究项目从现成的环丙醇开始：三元环化合物，像弹簧一样张紧，据说具有环张力。打开三元环的反应通过释放这种环张力而完成。Cha实验室开发了这些环丙醇的显著改进的制备。 他们正在开发环丙醇的新反应，以构建可能具有有用药用特性的更复杂分子。 这个项目是一个很好的培训基地，为年轻的科学家，从本科研究人员到博士后研究员，学习化学。该项目的具体目标包括设计新的化学反应，以促进重要结构基序或天然产物的简洁和环境友好的合成。重点放在高效率和收敛性，通过使用段偶联策略，其中两个大的片段连接在合成的后期阶段。 目前正在进行辛二烯酮和生物碱261C的简明全合成。 这些合成突出了新开发的合成方法的制备能力。 琥珀烯酮和生物碱261 C都是稀缺的天然产物，需要化学合成来评价其生物活性。 通过参与该项目，学生和博士后在有机方法开发，有机金属化学和天然产物合成方面得到培训。 他们为从事化学职业做好了充分的准备。

In this project, funded by the Chemical Synthesis Program of the Chemistry Division, Professor Cha of the Department of Chemistry at Wayne State University is investigating an efficient preparation of several molecular building blocks that have utility in organic and medicinal chemistry. The research project begins with readily available cyclopropanols: three-membered ring compounds that are tensioned like a spring and said to have ring strain. Reactions that open the three-membered rings are driven to completion by releasing this ring strain. The Cha laboratory developed a significantly improved preparation of these cyclopropanols. They are developing new reactions of cyclopropanols to build more complex molecules that may have useful medicinal properties. This project is an excellent training ground for young scientists, from undergraduate researchers to post-doctoral fellows, to learn about chemistry. The specific goals for the project include the design of new chemical reactions that facilitate concise and environmentally benign syntheses of important structural motifs or natural products. Emphasis is placed on high efficiency and convergence by use of segment coupling strategies, in which two large fragments are linked at a late stage in the synthesis. Concise total syntheses of suberosenone and alkaloid 261C are underway. These syntheses highlight the preparative power of the newly developed synthetic methods. Suberosenone and alkaloid 261C are both scarce natural products, and chemical syntheses are necessary to evaluate their biological activity. Through participation in this project, students and postdocs are trained in organic methods development, organometallic chemistry and natural product synthesis. They are well prepared for careers in chemistry.