Asymmetric Synthesis and Novel Transformations of 2-Oxetanones

2-氧杂环丁酮的不对称合成和新颖转化

• 批准号: 0104457
• 负责人: Daniel Romo
• 金额: $ 36.05万
• 依托单位: Texas A&M Research Foundation
• 依托单位国家: 美国
• 项目类别: Standard Grant
• 财政年份: 2001
• 资助国家: 美国
• 起止时间: 2001-08-15 至 2004-07-31
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=0104457&HistoricalAwards=false
• 关键词: Asymmetric; Synthesis; Novel; Transformations; Oxetanones

Professor Daniel Romo in the Department of Chemistry at Texas A&M University is supported by the Organic and Macromolecular Chemistry Program for his development of concise and practical enantioselective syntheses of beta-lactones via nucleophile catalyzed aldol-lactonizations (NCALs) of ketenes and aldehydes. Novel transformations of these beta-lactones to form various heterocyclic structures will be explored. The utility of the intramolecular NCAL reaction will be illustrated by the total synthesis of a lactacystin analog and an enantioselective synthesis of the natural product, brefeldin A. Mechanistic studies on the NCAL reaction will be carried out using REACT IR and 1H NMR.With the support of the Organic and Macromolecular Program, Professor Romo is developing novel methods by which certain highly strained organic compounds can be prepared with precise control of their three-dimensional structure. These compounds serve as intermediates which can be further converted to more complex products, many of which are share similar structural features with pharmacologically active compounds.

德克萨斯a&m大学化学系的Daniel Romo教授通过亲核试剂催化烯酮和醛酮的醛缩内酯化（NCALs），开发了简洁实用的-内酯对映选择性合成方法，得到了有机和大分子化学项目的支持。这些β -内酯形成各种杂环结构的新转化将被探索。分子内NCAL反应的效用将通过乳糖蛋白酶类似物的全合成和天然产物brefeldin a的对映选择性合成来说明。NCAL反应的机理研究将使用REACT IR和1H NMR进行。在有机和大分子项目的支持下，Romo教授正在开发新的方法，通过这种方法可以精确控制某些高度紧张的有机化合物的三维结构。这些化合物作为中间体，可以进一步转化为更复杂的产物，其中许多与药理活性化合物具有相似的结构特征。