Application of Cascade Processes for the Synthesis of Polycyclic Ring Systems

这项研究的重点有三个方面。首先，将使用一个新的[4+2]-环加成-重排序列来设置顶盖生物碱骨架的ABCe环核。其次，采用硫离子/N-酰亚胺离子串联环化策略合成了脱乙基亚叶基亚甲基中的吡咯并[2，3-d]咔唑环状骨架。第三，过渡金属催化的乙酰重氮乙酰胺的环化反应将作为一种合成包括士的宁在内的生物碱的途径进行研究。有了这个续展奖，有机和高分子化学计划正在支持埃默里大学化学系的阿尔伯特·帕德瓦博士的研究工作。帕德瓦教授将专注于开发串联或级联的方法，以便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、类卡宾或周环过程的组合将导致制备具有有趣生物学特性的结构多样化的合成靶标。这项研究对研究生的培养和与制药行业相关的方法论的发展具有更广泛的影响。

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.