Asymmetric Umpolung Aldehyde Reactions

不对称醛醛反应

• 批准号: 7120582
• 负责人: Tomislav Rovis
• 金额: $ 25.56万
• 依托单位: COLORADO STATE UNIVERSITY
• 依托单位国家: 美国
• 财政年份: 2005
• 资助国家: 美国
• 起止时间: 2005-09-05 至 2009-08-31
• 项目状态: 已结题
• 来源: https://reporter.nih.gov/project-details/7120582
• 关键词: acetylcholine; aldehydes; angiogenesis inhibitors; antineoplastics; catalyst; chemical bond; chemical group; chemical reaction; chemical substitution; chemical synthesis; drug design /synthesis /production; method development; molecular polarity; neurotransmitter antagonist; nicotinic receptors; stereochemistry; stereoisomer

The proposed work outlines an investigation into the design of processes used to form congested, multiply substituted bonds by taking advantage of a functional group's reversal of polarity. The reactions under investigation will rely on the use of catalytic amounts of a chiral source. Once a foundation for the key reactivity has been laid, we will turn our attention of applying this research to the rapid and stereoselective synthesis of a number of biologically active targets. Azaspirene is a novel angiogenesis inhibitor, a potential target for anti-cancer agents. Asparagamine A is a potent nicotinic acetylcholine receptor antagonist. Its stereochemically dense, polycyclic structure provides an incentive for us to develop a better, more efficient approach to these molecules. Lastly, we hope to develop a general approach to controlling absolute stereochemistry in a subfield of reactions that utilize radicals to form new bonds. Accomplishing this feat would open new vistas in complex molecule assembly that could take advantage of the ability of radicals to sequence multiple chemical transformations in a single step.

拟议的工作概述了一个调查的设计过程中用于形成拥挤的，多取代的债券，利用一个官能团的极性反转。所研究的反应将依赖于使用催化量的手性源。一旦关键反应的基础已经奠定，我们将把我们的注意力应用这项研究的快速和立体选择性合成的一些生物活性的目标。氮杂螺烯是一种新型的血管生成抑制剂，是一种潜在的抗癌药物靶点。天冬酰胺胺A是一种有效的烟碱乙酰胆碱受体拮抗剂。它的立体化学密集的多环结构为我们开发更好，更有效的方法来处理这些分子提供了动力。最后，我们希望开发一种通用的方法来控制绝对立体化学的反应，利用自由基形成新的债券的子字段。完成这一壮举将为复杂的分子组装开辟新的前景，可以利用自由基在一个步骤中进行多种化学转化的能力。