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具有最重要的地位。这导致近年来人们对催化对映选择性合成的兴趣日益浓厚，特别是对于难以获得的四元立构中心。基于之前的初步研究，该研究项目最初将重点开发铱催化的 1,3-二羰基分子内不对称烯丙基烷基化反应。这将允许容易地获得具有邻位四级-三级立构中心的各种碳环。这种新方法随后将应用于 Aquilarabietic Acid H 的全合成，这是一种新型天然化合物，在初步研究中显示出抗抑郁特性。此外，然后将不对称分子内反应扩展到具有含碳环烯丙基部分的底物。这将使我们能够轻松获得类固醇和相关药物中常见的多环基序。