德斯-环氧-安菲迪诺利德N的选择性合成
Barry M Trost1, Wen-Ju Bai1, Craig E Stivala1
1Department of Chemistry , Stanford University , Stanford , California 94305-5080 , United States.
Journal of the American Chemical Society
|November 21, 2018
概括
研究人员使用多步骤方法成功合成了des-epoxy-amphidinolide N. 这项工作澄清了结构关系,表明安菲迪诺化N和碳化I可能是相同的化合物.
科学领域:
- 有机化学 有机化学
- 合成化学 合成化学
- 自然产品的合成自然产品的合成
背景情况:
- 氨基胺 N 是一种复杂的海洋天然产品,具有潜在的生物活性.
- 之前的综合努力在安装关键功能组和管理保护组方面遇到了挑战.
研究的目的:
- 为了实现des-epoxy-amphidinolide N.的总合成.
- 开发和完善合成策略,包括催化基-基合.
- 为了调查安菲迪诺利德N和卡本诺利德I的结构相同性.
主要方法:
- 多代总合成方法. 多代总合成方法.
- 内部分子催化- (Ru AA) 合用于碎片组装.
- 保护组的战略性使用,以实现高效的合成.
- 晚期功能化,包括环氧化和二化.
- 计算分析和13C核磁共振光谱用于结构阐明.
主要成果:
- 在22个最长的线性步骤和33个总步骤中成功合成了des-epoxy-amphidinolide N.
- 克服二化中的挑战,并在三代合成物中保护群体策略.
- 提高了Ru AA合反应的效率和可扩展性.
- 通过计算方法识别安菲迪诺利德N内部的结合桥.
结论:
- 通过一种融合策略,完成了des-epoxy-amphidinolide N的总合成.
- 该研究强调了合成方法的演变,特别是Ru AA合和保护集团管理.
- 对比的NMR分析强烈表明,安菲迪诺利德N和卡本诺利德I可能是相同的化合物.
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