一种通用和可扩展的方法,以致于使用C2-替代性亚二烯酸丰富的C2-替代性亚二烯酸,使用基拉尔-丁硫胺
Daniel Zelch1, Christopher M Russo1, Kirsten J Ruud2
1Department of Chemistry, Villanova University, Villanova, Pennsylvania 19085, United States.
The Journal of organic chemistry
|September 30, 2024
概括
一种新的三步方法使用奇拉性 tert-butanesulfinamides 来制造多种C2 替代性亚齐丁丁. 这种方法为医药化学应用提供了以前难以捉摸的化产品.
科学领域:
- 有机化学 有机化学
- 药用化学 医学化学
- 合成化学 合成化学
背景情况:
- 在生物过程中,含有的环异循环对生物过程至关重要.
- 丰富Enantio的小型性异环的生产,特别是阿提丁,仍然是一个合成的挑战.
- 缺少C2替代性亚齐丁的一般和立体选择性方法.
研究的目的:
- 开发一种通用和立体选择性的方法来合成C2替代的亚齐丁丁.
- 为了利用廉价的合 tert-butanesulfinamides 进行不对称的诱导.
- 为医药化学提供一个可扩展的路径,以获得对抗纯亚二烯的药物化学.
主要方法:
- 这是一种三步合成,采用了奇拉性三丁硫胺和1,3-bis-电友性3-甲.
- 基拉尔诱导产生具有各种功能组 (,乙烯,,,基) 的C2替代性亚二烯.
- 格拉姆尺度合成和净化受保护的亚齐丁丁产品.
主要成果:
- 合成了11种不同的C2替代性亚兹提丁产物.
- 该方法在三个步骤中实现了44%的产量,其二聚体比为85:15.
- 可分离的二聚体产生了对抗纯亚丁胺产物,证明了可扩展性和适用性.
结论:
- 开发的方法提供了一种通用和立体选择性途径,以获得C2替代的亚齐丁丁.
- 合成的阿提丁可以很容易地被剥离保护和衍生,在药物化学中很有用.
- 这项工作解决了在获取有价值的合性亚齐丁丁构建块方面存在的重大瓶.
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