齐墩果酸A环与C环内酯衍生物的设计合成
收稿日期: 2015-09-01
修回日期: 2015-11-27
网络出版日期: 2015-12-07
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
Received date: 2015-09-01
Revised date: 2015-11-27
Online 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
俞飞 , 郑永祥 , 彭逸云 , 周德敏 , 肖苏龙 . 齐墩果酸A环与C环内酯衍生物的设计合成[J]. 有机化学, 2016 , 36(3) : 512 -519 . DOI: 10.6023/cjoc204509001
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
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