Synthesis of Cyclic Amino Acids Aiming at Elucidation of Neurotransmission Mechanism

环状氨基酸的合成旨在阐明神经传递机制

基本信息

批准号：
09672293
负责人：
NAITO Takeaki
金额：
$ 2.11万
依托单位：
Kobe Pharmaceutical University
依托单位国家：
日本
项目类别：
Grant-in-Aid for Scientific Research (C)
财政年份：
1997
资助国家：
日本
起止时间：
1997 至 1999
项目状态：
已结题

来源：
https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-09672293/
关键词：
neurotransmission mechanism Kainic acid amino acid radical thiophenol cyclization dipolar cycloaddition

项目摘要

Aiming at elucidation of neurotransmission mechanism involving amino acids, we started to develop a novel cyclization reactions suitable for the practical synthesis of cyclic amino acids which would be employed as crucial tools for the mechanistic study on neurotransmitters. Thus, ecological thiyl radical addition-cyclization of carbon multiple bonds and stannyl radical addition-cyclization of the carbonyl group have been proved to be potential synthetic method for the cyclic amino acids.1. Thiyl Radical Addition-Cyclization and its Application to the Synthesis of Cyclic Amino AcidsReadily available oxime ethers were subjected to thiyl radical addition-cyclization to give the adjacently functionalized cyclic compounds which were effectively converted into carbocyclic and heterocyclic amino acids. Asymmetric synthesis of (-)-α-kainic acid was achieved by applying newly found thiyl radical addition-cyclization-elimination reacting using a catalytic amount of thiophenol.2. 1,3-Dipolar Cycloaddition of Nitrone and its Application to the Synthesis of Cyclic Amino AcidsCombination of 1,3-dipolar cycloaddition of nitrones to chiral olefin and the following ring conversion were successfully applied the synthesis of azimic acid which is component of macrolide amino lactone, azimine, and expected to be active in central nervous system.3. Stannyl Radical Addition-Cyclization and its Application to the Synthesis of Cyclic Amino acids.We developed stannyl radical addition-cyclization of oxime ethers connected with the carbonyl groups and application to the synthesis of cyclic amino acids and the related compounds such as (-)-balanol.

为了阐明涉及氨基酸的神经传递机制，我们开始开发一种新型的环化反应，适合于实际合成环状氨基酸，该反应将用作神经递质机械研究的关键工具。这就是事实证明，碳多键和Stannyl自由基添加环化的生态硫基自由基添加环化已被证明是环状氨基酸的潜在合成方法。1。硫基自由基的添加循环及其在合成环状氨基酸的氧电情中的合成中进行了硫基自由基添加循环，从而使相邻功能化的循环化合物有效地转化为碳酰基酰基酰基和异地氨基酸。通过施加新发现的硫基自由基添加环化 - 使用催化量的硫酚2来实现（ - ） - α-甲酸的不对称合成。2。 1,3-Dipolar Cycloaddition of Nitrone and its Application to the Synthesis of Cyclic Amino Acids Combination of 1,3-Dipolar Cycloaddition of nitrones to chiral olefin and the following ring conversion were successfully applied the synthesis of azimic acid which is component of macrolide amino lactone, azimine, and expected to be active in central nervous system.3. Stannyl自由基添加环化及其在环状氨基酸的合成中的应用。我们开发了与羰基相关的氧乙醇的Stannyl自由基添加环化，并应用于循环氨基酸的合成和相关化合物（例如（ - ） - Balanol。