赫尔库林B和C的总合成
Xu Zhu1, Christopher C McAtee1, Corinna S Schindler1
1Willard Henry Dow Laboratory, Department of Chemistry , University of Michigan , 930 North University Avenue , Ann Arbor , Michigan 48109 , United States.
Journal of the American Chemical Society
|February 15, 2019
概括
研究人员使用l-tyrosine衍生的diketopiperazine开发了一种新的合成途径来获得herqulines B和C. 这种方法采用关键降解来将真菌环素类似物转化为赫尔库林结构图案.
科学领域:
- 有机合成
- 自然产品化学
- 医学化学
背景情况:
- 赫库林B和C是具有复杂结构的生物活性天然产品.
- 现有的合成方法往往耗时且产量低.
- 作为一种由l-tyrosine衍生而来的二甲基氨酸,它与herqulines具有结构上的相似性,这表明它有可能成为一种合成前体.
研究的目的:
- 为B和C线开发一种高效的新型合成策略.
- 作为一个关键的起始材料,使用一个mycocyclosin模拟物.
- 建立一个可靠的方法来访问赫尔库林核心结构.
主要方法:
- 使用一系列选择性还原反应来改变mycocyclosin模拟物的氧化状态.
- 使用高价介导的脱氧化来启动转化.
- 使用分子内源实现定向的伯奇降解.
- 应用铁催化还原用于皮佩拉环修饰.
主要成果:
- 从l-tyrosine衍生的二甲基素前体中成功合成了herqulines B和C.
- 证明了压力比系统的选择性转化为herqulines的特征性1,4-二基因.
- 实现了皮佩拉氧化状态的有效修改.
结论:
- 报告的合成方法提供了有效的B和C线路.
- 这一策略强调了在天然产品合成中使用菌环类的实用性.
- 开发的方法为访问相关化学结构提供了有价值的工具.
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