亚夫拉和14-亚夫拉的总合成
Hailong Li1, Qifeng Chen1, Zhaohong Lu1
1State Key Laboratory of Bioorganic and Natural Products Chemistry, Collaborative Innovation Center of Chemistry for Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.
Journal of the American Chemical Society
|December 10, 2016
概括
研究人员首次完成了阿弗拉瓦和14-亚弗拉的综合合成. 关键步骤包括AlI3促进的普林斯循环和结构组装的先进合反应.
科学领域:
- 有机化学
- 自然产品合成
- 医学化学
背景情况:
- 印度醇二烯酸是一种具有显著生物活性的复杂天然产品.
- 阿弗拉瓦和14-亚弗拉是这种类型的硬质要求很高的成员,这给合成带来了挑战.
- 之前的合成努力还没有完全合成这些特定的化合物.
研究的目的:
- 实现阿弗拉瓦和14-亚弗拉的第一个完整合成.
- 开发新型合成策略,用于制造无菌阻碍的二.
- 在组装复杂的分子结构中探索特定反应的实用性.
主要方法:
- 使用 (III) (AlI3) 促成的基Prins循环形成核心结构.
- 采用电循环-芳香化序列来构建替代的基.
- 应用Stille-Migita合组装四替代的烯酸.
- 纳入基和基C-O键的后期减少裂变.
主要成果:
- 成功合成了阿弗拉瓦 (6) 和14-亚弗拉 (8).
- 在构建复杂图案方面证明了AlI3促进的Alkyne Prins循环的有效性.
- 建立了高效的组装高度替代的芳香和油脂系统的路线.
- 实现后期功能组操纵以产生目标天然产品.
结论:
- 首次成功完成了阿夫拉瓦和14- 亚弗拉的总合成.
- 开发的合成策略提供了一个可靠的平台来获取复杂的乙烯.
- 这项工作扩大了合成工具包,用于制造无菌拥挤的天然产品.
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