Synthesis Driven by Release of Ring Strain

环应变释放驱动的合成

• 批准号: 1665331
• 负责人: Charles Winter
• 金额: $ 45万
• 依托单位: Wayne State 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=1665331&HistoricalAwards=false
• 关键词: Synthesis; Driven; Release; Ring; Strain; Synthesis; Driven; Release; Ring; Strain

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.

在该项目中，由化学部的化学合成计划资助，韦恩州立大学化学系的CHA教授正在研究有效的几个分子构建块，这些分子构建块在有机和药物化学方面具有实用性。 研究项目始于随时可用的环丙醇：三元的环化合物，它们像弹簧一样张紧，据说具有环应变。打开三元环的反应通过释放该环应变将其驱动到完成。 CHA实验室开发了这些环丙醇的制备明显改善。 他们正在开发环丙醇的新反应，以建立可能具有有用药用特性的更复杂的分子。 该项目是年轻科学家的良好培训理由，从本科研究人员到博士后研究员，以了解化学。该项目的具体目标包括设计新的化学反应，这些反应促进了重要的结构基序或天然产品的简洁和环境良性合成。通过使用片段耦合策略，重点放在高效率和收敛上，其中两个大片段在合成的后期链接。 subersoinone和生物碱261c的简洁总合成正在进行中。 这些合成突出了新开发的合成方法的制备能力。 Suberosenone酮和生物碱261c都是稀缺的天然产物，化学合成对于评估其生物学活性是必要的。 通过参与该项目，学生和博士后接受了有机方法开发，有机金属化学和自然产品合成的培训。 他们为化学职业做好了充分的准备。