总合成的 (-) - 卡利西菲林 N
Artem Shvartsbart1, Amos B Smith
1Department of Chemistry, Laboratory for Research on the Structure of Matter, and Monell Chemical Senses Center, University of Pennsylvania , Philadelphia, Pennsylvania 19104, United States.
Journal of the American Chemical Society
|December 11, 2013
概括
复杂的达夫尼菲林 (Daphniphyllum) 类化合物 (-) - 卡利西菲林N的总合成现在已经完成. 这一成就利用了先进的合成策略,包括立体选择性分子内迪尔斯-阿尔德反应和具有挑战性的化.
科学领域:
- 有机化学 有机化学
- 自然产品的合成自然产品的合成
- 药用化学 医学化学
背景情况:
- 达夫尼菲勒姆类化合物是一种具有潜在生物活性的复杂自然产品.
- (-) - - 素N是这个类家族的结构复杂的成员.
- 建立有效的合成路径到这些复杂的分子对于进一步的研究至关重要.
研究的目的:
- 为了实现第一个建筑复杂的Daphniphyllum类化合物 (-) -calyciphylline N.的首次完全合成.
- 开发和展示适用于复杂天然产品合成的新型合成方法.
主要方法:
- 该合成采用了基质控制的分子内迪尔斯-阿尔德反应,由乙化 (Et2AlCl) 促进.
- 关键步骤包括一个跨环的酸化和一个静态碳化,然后是纳扎罗夫循环.
- 一个完全替代的联二烯的二选择性化是一个关键的,高风险的步骤.
主要成果:
- 成功完成了 (-) - - 卡利西菲林N 的总合成.
- 合成路线在关键转换中显示出高的立体选择性.
- 这项研究强调了构建类化合物的复杂多环核的可行性.
结论:
- 总合成的 (-) -calyciphylline N 提供了一个有价值的路径,这个复杂的天然产品.
- 开发的合成策略可以应用于合成其他Daphniphyllum类化合物.
- 这项工作为有机合成和天然产品化学领域做出了贡献.
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