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努力实现图加辛A的总合成

Yang Liu^1,2, Yi Liu³, Jun Liu^1,2,4

¹State Key Laboratory of Environmental Chemistry and Eco-toxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, Beijing 100085, China.

Organic letters

|November 15, 2024

概括

研究人员报告说,他们首次实现了 thuggacin A 的融合总合成,thugacin A 是一种具有抗结核活性的多基类抗生素. 合成了一种类似物 (2),对结核病有中度活性.

科学领域:

有机化学有机化学
药用化学医学化学
化学生物学化学生物学

背景情况:

图加A是一种17个分子的多基类抗生素,具有已证明的抗结核活性.
之前没有报道过 thuggacin A 的总合成情况.
开发合成途径以复杂的天然产品对于药物发现和开发至关重要.

研究的目的:

为了实现第一个汇聚的Thuggacin A.A.的总合成.
开发和应用新的合成方法来构建 thuggacin A 框架.
合成和评估对抗结核活动的thuggacin A的类似物.

主要方法:

收合成策略. 收合成策略.
关键反应包括一级联 thiazole 形成,埃文斯 syn-aldol,Mukaiyama 非对称 aldol,有机促进的减小,Shiina 巨乳化,和环氧环与开放.
一个三甲基乙氧甲基 (SEM) 衍生类型的enantioselective合成 (2).

主要成果:

成功合成 thuggacin A 模拟物的融合总合成 2.
合成在18个最长的线性步骤中完成,总产量为2.0%.
合成的模拟物2表现出中度抗结核活性,最小抑制度 (MIC) 为320μg/mL.

结论:

开发的合成途径为获取 thuggacin A 和其类似物提供了一条可行的途径.
综合强调了在构建复杂的多基基结构时使用的关键反应的实用性.
类似物2的适度抗结核活性需要进一步研究和优化,以寻找潜在的治疗应用.

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