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整体合成 (+) - 普勒莫提林
Elliot P Farney1, Sean S Feng1, Felix Schäfers1
1The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology , Pasadena, California 91125, United States.
Journal of the American Chemical Society
|January 12, 2018
概括
使用关键立体选择反应,开发了抗生素 (+) - 斑素的18步合成方法. 这一突破可以为未来的治疗应用创造新型木素抗生素.
科学领域:
- 有机合成
- 医学化学
- 抗生素的开发
背景情况:
- 这是一种具有独特四环二烯核的天然抗生素.
- 现有的合成途径往往是漫长而复杂的.
- 开发高效的合成策略对于获取新型类似物至关重要.
研究的目的:
- 揭示一种新且高效的抗生素 (+) - 斑素的18步合成方法.
- 使用先进的合成方法建立关键立体中心.
- 为新型基于mutilin的抗生素提供一个平台.
主要方法:
- 采用了一个18步合成序列.
- 使用 (SmI2) 介导的循环制造来制造八个环.
- 实施了立体特异的跨环形[1,5]-原子转移以控制C10立体化学.
主要成果:
- 在18个步骤中成功合成 (+) - 斑素.
- 在SmI2介导的循环化步骤中实现了高立体选择性.
- 通过相同的策略证明了制备 (+) -12-epi-pleuromutilin的能力.
结论:
- 开发的合成路由是高效和立体控制.
- 关键的循环和转移反应是强大的.
- 这种合成方法有助于探索新的木林抗生素衍生物.
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