肯多米辛的总合成:一个宏-C-糖化方法
Yu Yuan1, Hongbin Men, Chulbom Lee
1Department of Chemistry, Princeton University, Princeton, NJ 08544-1009, USA.
Journal of the American Chemical Society
|November 13, 2004
概括
具有抗生素和抗癌性质的强效安萨素kendomycin的总合成是使用一种新的宏糖化反应实现的. 这一突破使得肯多米辛的进一步研究成为可能.
科学领域:
- 有机化学 有机化学
- 药用化学 医学化学
- 自然产品的合成自然产品的合成
背景情况:
- 肯多米辛是一种新型的多基酸衍生安萨米辛,具有显著的生物活性.
- 它作为内甲素受体的对抗剂和素受体的激动剂.
- 肯多米辛表现出强大的抗生素特性和对癌症细胞系的细胞静止作用.
研究的目的:
- 为了实现第一个Kendomycin的enantioselective总合成.
- 开发和应用一种用于复杂分子合成的新型宏糖化反应.
- 建立组装肯多米辛支架的高效方法.
主要方法:
- 用Friedel-Crafts类型的环闭来形成宏循环并建立C-糖化链接.
- 一种新的巨糖化反应是合成的关键步骤.
- ((0)) 催化苏苏基-米亚乌拉交叉合被用来构建第二个宏循环.
主要成果:
- 肯多米辛的总合成成功地以高的反选择性完成.
- 关键的宏糖化反应产生了宏循环作为一个单一的立体同位素在良好的产量.
- 合成利用了随时可用的构建块,以模块化方式组装在一起.
结论:
- 已经建立了第一个对肯多米的全合成.
- 开发的合成策略,特别是新型的巨糖化,为肯多米辛及其类似物提供了可行的途径.
- 这种合成为探索肯多米辛的治疗潜力开辟了道路.
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