The Aza-variant of the Photochemical Oxa-di-pi-methane Rearrangement for the Synthesis of Alkaloids

光化学 Oxa-di-pi-甲烷重排的 Aza 变体用于合成生物碱

• 批准号: 0079288
• 负责人: Cynthia McClure
• 金额: $ 35.5万
• 依托单位: Montana State University
• 依托单位国家: 美国
• 项目类别: Standard Grant
• 财政年份: 2000
• 资助国家: 美国
• 起止时间: 2000-08-01 至 2003-07-31
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=0079288&HistoricalAwards=false
• 关键词: Aza; variant; Photochemical; Oxa; di

The focus of this research is the development of the aza-variant of the oxa-di-pi-methane photochemical rearrangement as a new synthetic method for the preparation of nitrogen heterocycles. The rearrangement of azabicyclo[2.2.2]-octenones and azabicyclo[3.2.2]-nonenones is expected to provide tricyclic products in which the 3-member ring can be cleaved stereoselectively to give pyrrolizidines, indolizidines or tropanes. New methodologies based on the Diels-Alder reaction are being developed to synthesize the requisite photoprecursors and the attachment of photoprecursors and photosensitizers to resins will be explored as a means for ready isolation and functionalization of photoproducts. With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Dr. Cynthia K. McClure of the Department of Chemistry at Montana State University. Professor McClure will focus her work on developing photochemical methods for the production of nitrogen heterocycles. The synthetic targets are compounds with interesting biological properties and the work should have broader impact in the pharmaceutical industry. The research provides an excellent training ground for the education of undergraduate and graduate students.

本研究的重点是开发一种新的氮杂环合成方法，即oxa-di-pi-甲烷光化学重排的aza变体。氮杂环[2.2.2]-辛烯酮和氮杂环[3.2.2]-壬烯酮的重排有望提供三环产物，其中3元环可以立体选择性地劈裂得到吡咯烷类、吲哚嘧啶类或tropanes。基于Diels-Alder反应的新方法正在被开发用于合成所需的光递质，并且将光递质和光敏剂附着在树脂上作为光产物的快速分离和功能化的手段将被探索。有了这个奖项，有机和大分子化学项目支持蒙大拿州立大学化学系的辛西娅·k·麦克卢尔博士的研究。麦克卢尔教授将专注于开发生产氮杂环的光化学方法。合成目标是具有有趣的生物学特性的化合物，这项工作将在制药工业中产生更广泛的影响。该研究为本科生和研究生的教育提供了良好的训练基地。