Application of Cascade Processes for the Synthesis of Polycyclic Ring Systems

级联工艺在多环体系合成中的应用

• 批准号: 0132651
• 负责人: Albert Padwa
• 金额: $ 40.8万
• 依托单位: Emory University
• 依托单位国家: 美国
• 项目类别: Continuing Grant
• 财政年份: 2002
• 资助国家: 美国
• 起止时间: 2002-01-01 至 2005-12-31
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=0132651&HistoricalAwards=false
• 关键词: Application; Cascade; Processes; Synthesis; Polycyclic

The foci of this research are three-fold. First , a novel [4+2]-cycloaddition -rearrangement sequence will be used to set the ABCE cyclic core of the aspidosperma alkaloid skeleton. Second, a tandem thionium/N-acyliminium ion cyclization strategy will be used to afford the pyrrolo[2,3-d]carbazole ring framework found in deethylibophyllidene. Third, the transition metal mediated cyclization of acetylenic diazoketoamides will be studied as a route to the synthesis of a number of alkaloids including strychnine.With this Renewal award, the Organic and Macromolecular Chemistry Program is supporting the research efforts of Dr. Albert Padwa of the Department of Chemistry at Emory University. Professor Padwa will focus his work on the development of tandem, or cascade, methods for the formation of several carbon-carbon bonds and/or rings systems in a single operation. Using combinations of cationic, anionic, radical, carbenoid or pericyclic processes will lead to the preparation of structurally diverse synthetic targets possessing interesting biological properties. The research has broader impact for the training of graduate students and for the development of methodology pertinent to the pharmaceutical industry.

这项研究的重点有三个方面。 首先，一个新的[4+2]-环加成-重排序列将被用来设置盾子草生物碱骨架的ABCE环状核心。 第二，串联的硫鎓/N-酰基咪唑离子环化策略将用于提供在deethylbophyllidene中发现的吡咯并[2，3-d]咔唑环框架。 第三，过渡金属介导的炔属重氮酮酰胺的环化反应将作为合成包括士的宁在内的一些生物碱的途径进行研究。有了这个更新奖，有机和大分子化学计划支持埃默里大学化学系的Albert Padwa博士的研究工作。 Padwa教授将专注于开发串联或级联方法，用于在一次操作中形成几个碳-碳键和/或环系统。使用阳离子、阴离子、自由基、类卡宾或周环方法的组合将导致制备具有感兴趣的生物学性质的结构多样的合成靶。 该研究对研究生的培养和制药工业相关方法的发展具有更广泛的影响。