使用化学网络分析启发的策略,对迪特尔类类阿库丁的总合成
Kyle R Owens1, Shelby V McCowen1, Katherine A Blackford1
1Department of Chemistry , University of California , Berkeley , California 94720 , United States.
Journal of the American Chemical Society
|July 6, 2019
概括
这项研究报告了第一个全合成的arcutinidine,一个复杂的二类化物. 这种新型合成策略利用独特的循环添加和合反应来构建丁胺复杂的桥梁框架.
科学领域:
- 有机化学
- 自然产品合成
- 医学化学
背景情况:
- 阿库丁丁和相关的阿库丁丁类二类类物质具有复杂的多环形桥梁结构,具有独特的连接性.
- 了解这些天然产品的合成对于探索它们的潜在生物活动和生物合成途径至关重要.
研究的目的:
- 为了实现第一个全合成的arcutinidin.
- 开发新的合成方法来构建复杂的桥梁化物框架.
- 为研究相关二甲之间的生物合成关系提供基础.
主要方法:
- 化学网络分析以确定简化的回合成断路.
- 一个前所未有的oxopyrroliumDiels-Alder循环添加形成一个关键的四环中间体.
- 一个二重选择性的氧化脱氧化/循环添加序列.
- 二氧化 (SmI2) 介导的碳-碳合组装桥架.
主要成果:
- 顺利完成阿库丁丁的总合成.
- 用于构建复杂的多环系统的新型氧迪尔斯-阿尔德反应的演示.
- 建立关键的C-C键形成,以造桥梁式二类化物骨架.
结论:
- 开发的合成途径提供了有效的阿库丁和其类似物.
- 合成策略强调了回合成分析和新型循环添加反应在天然产品合成中的力量.
- 这项工作为未来对阿库坦和相关二类化合物生物合成的研究奠定了基础.
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