夸德里格米因C和心理素的全合成
Alec D Lebsack1, J T Link, Larry E Overman
1Department of Chemistry, 516 Rowland Hall, University of California Irvine, California 92697-2025, USA.
Journal of the American Chemical Society
|August 1, 2002
概括
首次实现了四胺C和心理素的总合成. 这些复杂的多罗利迪诺因多林类化合物是使用新型合成策略构建的,证实了它们的结构.
科学领域:
- 有机化学 有机化学
- 总的综合 总的综合
- 化物化学 化物化学
背景情况:
- 聚烯利丁胺类化合物代表了一类复杂的自然产品.
- 之前的合成努力并没有接触到这个家族的更高阶成员.
研究的目的:
- 报道了第一个四胺C和psycholine的总合成.
- 开发高效的合成路径,使复杂的多罗利迪诺因多林类化合物.
主要方法:
- 合成开始于由氧醇和异氨酸衍生出来的美索基蒙南丁.
- 关键步骤包括Stille交叉合和催化不对称Heck循环.
- 该策略涉及到将一个中位元前体去对称,以安装立体中心.
主要成果:
- 合成了四氧化物C (1) 和心理素 (3).
- 四素C的合成是在19个线性步骤中完成的,总产量为2%.
- 一个关键的中间体得到了62%的产量和90%的反体过剩.
结论:
- 总合成严格证实了四素C的相对和绝对配置.
- 开发的合成方法提供了更高阶的多聚罗利迪诺因多林化物.
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