在FD-891的Enantioselective总合成
Michael T Crimmins1, Franck Caussanel
1Department of Chemistry, Venable and Kenan Laboratories of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599-3920, USA. crimmins@email.unc.edu
Journal of the American Chemical Society
|March 9, 2006
概括
在21个步骤中实现了FD-891的酶选择性合成. 关键反应包括阿尔多尔添加和交叉转移,为这个复杂的分子建立了关键的立体中心.
科学领域:
- 有机化学 有机化学
- 合成化学 合成化学
- 药用化学 医学化学
背景情况:
- FD-891是一种复杂的有机分子,具有显著的治疗潜力.
- 有效和立体选择性合成路径对其发展至关重要.
- 以前的合成方法可能在产量或立体控制方面存在局限性.
研究的目的:
- 开发一种新且高效的FD-891.1酶选择合成方法.
- 建立一个强大的合成策略,用于构建分子的立体中心.
- 为了实现FD-891的可扩展生产,用于进一步的研究.
主要方法:
- 使用了来自N-acylthiazolidinethiones的化乙烯酸盐的阿尔多尔添加剂.
- 采用一个关键的交叉转化反应来连接分子碎片.
- 纳入了最后阶段的朱莉亚精加工,用于最终的子单元组装.
主要成果:
- 实现了FD-891.1.的酶选择性合成.
- 最长的线性序列包括21个步骤.
- 在10个立体中心中成功建立了6个,使用关键的阿尔多尔添加反应.
结论:
- 开发的合成策略对FD-891.9的enantioselective合成有效.
- 关键的阿尔多尔添加反应是控制立体化学的关键.
- 交叉转移和朱莉亚精的结合有效地组装了分子框架.
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