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发育以及药物化学中仍然具有最重要的重要性。近年来，这导致人们对催化性，对映选择性合成的兴趣增加，尤其是在难以进入的第四纪立体中心。基于先前的初步研究，研究项目最初将着重于开发1,3-二碳苯子的虹膜催化，分子内，不对称的烯丙基烷基化反应。这将可以轻松访问带有近季赛立体观念的各种碳循环。然后将这种新方法应用于Aquilarabietic Acid H的总合成，这是一种新型的天然化合物，在初步研究中显示抗抑制性特性。此外，然后将不对称的分子内反应扩展到具有含有碳纤维的烯烃部分的底物。这将使您可以轻松获取类固醇和相关药物中常见的多环基序。