Development of Iridium-catalyzed, intramolecular, asymmetric allylic alkylation reactions and their application towards the total synthesis of Aquilarabietic Acid H

铱催化分子内不对称烯丙基烷基化反应的发展及其在水木香枞酸 H 全合成中的应用

• 批准号: 390789510
• 负责人: Dr. Sebastian Lackner
• 金额: --
• 依托单位: Division of Chemistry and Chemical Engineering
• 依托单位国家: 德国
• 项目类别: Research Fellowships
• 财政年份: 2017
• 资助国家: 德国
• 起止时间: 2016-12-31 至 2018-12-31
• 项目状态: 已结题
• 来源: https://gepris.dfg.de/gepris/projekt/390789510?language=en
• 关键词: Development; Iridium; catalyzed; intramolecular; asymmetric

Synthetic organic chemistry continues to be of highest importance within drug discovery and development, as well as medicinal chemistry. This led to increased interest in catalytic, enantioselective synthesis in recent years, particularly regarding difficult to access, quaternary stereocenters. Based on previous initial studies the research project will initially focus on developing an Iridium-catalyzed, intramolecular, asymmetric allylic alkylation reaction of 1,3-dicarbonyls. This would allow easy access to various carbocycles with vicinal quaternary-tertiary stereocenters. This new methodology is then to be applied to the total synthesis of Aquilarabietic Acid H, a novel natural compound that showed anti-depressant properties in initial studies. Further, the asymmetric, intramolecular reaction is then to be extended to substrates with carbocycle-containing allyl moieties. This would give easy access to polycyclic motifs commonly found in steroids and related pharmaceutical drugs.

合成有机化学在药物发现和开发以及药物化学中仍然是最重要的。这导致近年来对催化、对映选择性合成的兴趣增加，特别是难以获得的四元立体中心。基于先前的初步研究，该研究项目将首先集中于开发一种铱催化的1,3-二羰基的分子内不对称烯丙基烷基化反应。这样就可以很容易地得到具有相邻的第四-叔立体中心的各种碳环。这种新方法随后将被应用于Aquilarabietic Acid H的全合成，这是一种新的天然化合物，在最初的研究中显示出抗抑郁的特性。此外，不对称的分子内反应随后被扩展到含有碳环烯丙基的底物。这将使我们更容易接触到类固醇和相关药物中常见的多环基序。