Cascade Catalysis and its Application Towards the Synthesis of Bioactive Compound

级联催化及其在生物活性化合物合成中的应用

• 批准号: 8063006
• 负责人: Kerem Ozboya
• 金额: $ 2.81万
• 依托单位: COLORADO STATE UNIVERSITY
• 依托单位国家: 美国
• 财政年份: 2011
• 资助国家: 美国
• 起止时间: 2011-05-01 至 2014-04-30
• 项目状态: 已结题
• 来源: https://reporter.nih.gov/project-details/8063006
• 关键词: Amines; Benzoin; Biological Factors; Catalysis; Complex; Development; Folk Medicine; Goals; Knowledge; Lead; Methodology; Molecular Conformation; Organic Chemistry; Organic Synthesis; Protocols documentation; Reaction; Research; Route; Sodium Chloride; carbene; catalyst; cyclopentanone; new technology

DESCRIPTION (provided by applicant): The goal of this project is the discovery and development of new cascade reactions involving N-heterocyclic carbene catalysts. Currently, research has led to the discovery of a new Michael- Benzoin cascade for the formation of functionalized cyclopentanones in high yield and excellent diastereoselectivity and enantioselectivity. This cascade reaction uses both a secondary amine catalyst and a chiral triazolium salt developed in our labs. Higher yields and selectivity are achieved using this cascade methodology as opposed to a traditional, two-reaction protocol. In addition, this methodology has been applied towards the synthesis of Crescentin IV. This compound has been used in folk medicines of several cultures. We believe a concise and selective synthesis of this compound can be achieved using this new cascade methodology. This synthetic route should lend itself to the syntheses of related, bioactive compounds. The knowledge gained from the development of this reaction will then be applied to the discovery of new cascade reactions. Accomplishments in this field will then lead to the quick, efficient syntheses of medicinally important compounds. PUBLIC HEALTH RELEVANCE: Cascade catalysis is a growing field in organic chemistry that allows the efficient synthesis of complex compounds using multiple catalysts. We have applied this principle in the construction of complex cyclopentanones using simple starting materials. This new methodology will provide access to medicinally important molecules in a quick and selective manner.

描述(由申请人提供)：该项目的目标是发现和开发涉及N-杂环卡宾催化剂的新的级联反应。目前，研究已经发现了一种新的迈克尔-安息香级联反应，可以高产率地形成官能化的环戊酮，并具有良好的非对映选择性和对映选择性。这种级联反应同时使用了仲胺催化剂和我们实验室开发的手性三氮唑盐。与传统的双反应方案不同，使用这种级联方法可以获得更高的产率和选择性。此外，该方法学已应用于月桂素IV的合成。该化合物已用于几种文化的民间药物中。我们相信，使用这种新的级联方法可以实现这种化合物的简明和选择性的合成。这条合成路线将有助于合成相关的生物活性化合物。从该反应的发展中获得的知识将被应用于发现新的级联反应。这一领域的成就将导致快速、高效地合成具有重要药用价值的化合物。 与公众健康相关：级联催化是有机化学中一个不断发展的领域，它允许使用多种催化剂高效地合成复杂化合物。我们已将这一原理应用于用简单的起始原料合成复杂的环戊酮。这一新的方法将提供快速和选择性地获取医学上重要分子的途径。