补骨脂酚的化学与生物学研究进展

doi:10.6023/cjoc201408015

摘要/Abstract

补骨脂是一种传统的中国及印度民间草药, 可用于治疗多种疾病. 补骨脂酚是从补骨脂中提取分离的一种重要单萜类化合物, 它具有广泛的药理活性, 是一个具有开发潜力的药物先导化合物. 开展新颖高效的补骨脂酚合成研究对进一步开发其药学用途具有重要理论意义和应用价值. 补骨脂酚全合成的关键在于其季碳中心的构建. 目前已有众多小组发展不同的策略来完成这项工作, 如醚类的Claisen重排反应; 乙烯基铜试剂对α,β-不饱和羰基化合物的1,4-加成反应; 环氧硅基醚的环氧重排反应; 分子内重氮磺酸盐对C—H的插入反应; 铜催化的S_N2'型烯丙位取代反应; α,β-不饱和酰胺的α-烷基化反应以及烯丙基化反应. 介绍了近年来补骨脂酚的生理活性及其化学合成研究.

关键词: 补骨脂酚, 生理活性, 全合成, 季碳, 综述

Psoralea corylifolia (Linn.) has been used to treat a variety of diseases in both Chinese and Indian folkloric medicine. The moroterpene, bakuchiol, was isolated from the seeds of Psoralea corylifolia Linn. With a broad range of biological activities bakuchiol is considered as a leading compound for drug development. It is highly desirable to devise an efficient approach to access bakuchiol for further investigating its biologically relevant pathways. The key element in the total synthesis of bakuchiol relies on construction of the quaternary carbon stereocenter. This goal had been accomplished through several innovative strategies, such as Claisen rearrangement of geranyl enol ether, 1,4-addition of vinylcuprate species with α,β-unsaturated carbonyl compound, rearrangement of epoxy silyl ether, intramolecular diazosulfonate carbene insertion into a tertiary C—H bond, Cu-catalyzed S_N2'-type allylic substitution, α-alkylation of α,β-unsaturated amide, allylmetalation, and allylboration. In this review, bioactivities and various synthetic routes of bakuchiol are discussed.

Key words: bakuchiol, bioactivity, total synthesis, quaternary carbon, review

引用此文

黄莎华, 黄梦媛, 贾学顺, 洪然. 补骨脂酚的化学与生物学研究进展[J]. 有机化学, 2014, 34(12): 2412-2423.

Huang Shahua, Huang Mengyuan, Jia Xueshun, Hong Ran. Chemistry and Biology of Bakuchiol[J]. Chin. J. Org. Chem., 2014, 34(12): 2412-2423.

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