高等学校化学学报 ›› 2012, Vol. 33 ›› Issue (07): 1476-1480.doi: 10.3969/j.issn.0251-0790.2012.07.020

• 有机化学 • 上一篇    下一篇

Marinopyrrole A衍生物合成方法的优化

潘立立, 程春伟, 宋颢   

  1. 四川大学华西药学院, 成都 610041
  • 收稿日期:2011-11-08 出版日期:2012-07-10 发布日期:2012-07-10
  • 通讯作者: 宋 颢, 女, 博士, 讲师, 主要从事天然产物合成研究. E-mail: songhao@scu.edu.cn E-mail:songhao@scu.edu.cn
  • 基金资助:

    国家自然科学基金(批准号: 21002066)和四川大学青年教师基金(批准号: 2009SCU11181)资助.

Optimization of Synthetic Method of Marinopyrrole A Derivatives

PAN Li-Li, CHENG Chun-Wei, SONG Hao   

  1. West China School of Pharmacy, Sichuan University, Chengdu 610041, China
  • Received:2011-11-08 Online:2012-07-10 Published:2012-07-10

摘要: 以双醛化合物1为原料, 通过取代基保护、 分步加成、 氧化、 脱Ts(对甲苯磺酰基)、 氯代和脱甲基等反应, 以9步反应13%的总收率合成了苯环6位含氟取代的Marinopyrrole A衍生物12, 所合成化合物的结构经IR, 1H NMR, 13C NMR和HRMS分析确证. 分步加成和氧化的应用有效避免了原合成方法中环醚中间体3的生成, 提高了反应总收率, 为系列Marinopyrrole A 衍生物的合成提供了一种新方法.

关键词: Marinopyrrole A衍生物, 环醚中间体, 优化合成

Abstract: Marinopyrrole A, containing a novel structure with high halogenated bipyrrole, was found to exhibite antibacterrial activity against Methicillin-resistant staphylococcus aureus(MRSA), and against the human cancer cell(HCT-116). Owing to its low potency and high toxicity in vivo, the synthesis of Marinopyrrole A derivatives has become a new hot spot in natural products research.6-Flourobenzene of Marinopyrrole A was obtained by protection, addition step-by-step, oxidation, deprotection of the Ts group, chlorinated and deprotection of methyl group reactions from the starting material dialdehyde compound 1, and finally the yield was 13% after 9-step reactions. The structures of the compounds were confirmed by IR, 1H NMR, 13C NMR and HRMS. Especially, the cyclic ether intermediate 3, necessary in original way, was no longer formed using the addition step-by-step and oxidation, and the total yield was improved. The examination approach provides a new synthetic way for the series Marinopyrrole A derivatives.

Key words: Marinopyrrole A derivative, Cyclic ether intermediate, Optimization of synthesis method

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