有机化学 ›› 2016, Vol. 36 ›› Issue (3): 512-519.DOI: 10.6023/cjoc204509001 上一篇    下一篇

研究论文

齐墩果酸A环与C环内酯衍生物的设计合成

俞飞a, 郑永祥b, 彭逸云b, 周德敏b, 肖苏龙b   

  1. a 昆明理工大学医学院 昆明 650500;
    b 北京大学药学院 天然药物及仿生药物国家重点实验室 北京 100191
  • 收稿日期:2015-09-01 修回日期:2015-11-27 发布日期:2015-12-07
  • 通讯作者: 俞飞, 肖苏龙 E-mail:feiyuz8@163.com;slxiao@bjmu.edu.cn
  • 基金资助:

    天然药物及仿生药物国家重点实验室开放基金(No. K20150214)、昆明理工大学人才引进(No. KKSY201560002)资助项目.

Design and Synthesis of Oleanolic Acid Rings A and C Lactone Derivatives

Yu Feia, Zheng Yongxiangb, Peng Yiyunb, Zhou Deminb, Xiao Sulongb   

  1. a Medical Faculty, Kunming University of Science and Technology, Kunming 650500;
    b State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191
  • Received:2015-09-01 Revised:2015-11-27 Published:2015-12-07
  • Supported by:

    Project supported by the Open-Fund Program of the State Key Laboratory of Natural and Biomimetic Drugs (No. K20150214), the Scientific Research Foundation of Kunming University of Science and Technology (No. KKSY201560002).

齐墩果酸是一个五环三萜类天然产物, 具有多种生物活性和药理活性. 以齐墩果酸为起始原料, 采用间氯过氧苯甲酸以及过氧化脲等试剂进行其A环和C环内酯化修饰, 以较高收率获得了系列齐墩果酸A/C环内酯化衍生物. 所有产物均经1H NMR、13C NMR和高分辨质谱数据分析进行了结构确定, 其中有12个化合物为新化合物.

关键词: 齐墩果酸, Baeyer-Villiger反应, 内酯

Oleanolic acid (OA), a naturally occurring triterpene, was found to have a variety of biological and pharmacological properties. To expand its structural diversity, a series of oleanolic acid derivatives, including ring A and/or ring C expansion, were performed via Baeyer-Villiger reaction using m-CPBA and urea-hydrogen peroxide. The structures of all products were characterized by 1H NMR, 13C NMR and HRMS.

Key words: oleanolic acid, Baeyer-Villiger reaction, lactone