Reductive Radical Cyclizations for Heterocycle Synthesis

杂环合成的还原自由基环化

• 批准号: 240508776
• 负责人: Professor Dr. Jan Streuff
• 金额: --
• 依托单位: Institutionen för kemi
• 依托单位国家: 德国
• 项目类别: Research Grants
• 财政年份: 2013
• 资助国家: 德国
• 起止时间: 2012-12-31 至 2019-12-31
• 项目状态: 已结题
• 来源: https://gepris.dfg.de/gepris/projekt/240508776?language=en
• 关键词: Reductive; Radical; Cyclizations; Heterocycle; Synthesis

The development of modern and efficient methods for the synthesis of heterocyclic building blocks is of fundamental importance for the synthesis of natural products and drugs as well as industrial applications. The titanium(III)-catalyzed radical cyclizations that will be developed in this project will enable unconventional, flexible, and straightforward syntheses of central indole, pyrrole, indolizidine, and quinolizidine building blocks, as well as multifunctionalized pyridines. In addition, structural fragments such as 3-aminoindoles and 3-pyrroles will become directly available and can be derivatized in situ. Previously, these molecule classes were rarely employed in organic synthesis due to their instability and limited synthetic access. The applicability of the presented innovative cyclization methods will be demonstrated on highly efficient total syntheses of natural products such as isatisin A, mitragynin and mitragynin pseudoindoxyl. The successful completion of this project will further establish the titanium(III)-catalysis as a versatile method for heterocycle synthesis.

开发现代高效的杂环结构单元合成方法对于天然产物和药物的合成以及工业应用至关重要。该项目将开发的钛(III)催化自由基环化反应将能够非常规、灵活、直接地合成中心吲哚、吡咯、吲哚里西啶和喹里西啶结构单元以及多功能吡啶。此外，结构片段如3-氨基吲哚和3-吡咯将变得直接可用并且可以原位衍生化。此前，由于这些分子类别不稳定且合成途径有限，因此很少用于有机合成。所提出的创新环化方法的适用性将在天然产物（例如板蓝根A、帽柱木素和帽柱木素假吲哚酚）的高效全合成中得到证明。该项目的成功完成将进一步确立钛（III）催化作为杂环合成的通用方法。