Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (12): 2412-2423.DOI: 10.6023/cjoc201408015 Previous Articles     Next Articles

REVIEW

补骨脂酚的化学与生物学研究进展

黄莎华a,c, 黄梦媛b,c, 贾学顺b, 洪然c   

  1. a. 上海应用技术学院 化学与环境工程学院 上海 201418;
    b. 上海大学化学系 上海 200444;
    c. 中国科学院上海有机化学研究所 天然产物有机合成化学重点实验室 上海 200032
  • 收稿日期:2014-08-14 修回日期:2014-09-09 出版日期:2014-12-25 发布日期:2014-09-12
  • 通讯作者: 黄莎华 E-mail:shahua@sit.edu.cn
  • 基金资助:

    上海市高校青年教师培养计划(No.yyy11015)和国家自然科学青年基金(No.21402121)资助项目

Chemistry and Biology of Bakuchiol

Huang Shahuaa,c, Huang Mengyuanb,c, Jia Xueshunb, Hong Ranc   

  1. a. School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418;
    b. Department of Chemistry, Shanghai University, Shanghai 200444;
    c. CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
  • Received:2014-08-14 Revised:2014-09-09 Online:2014-12-25 Published:2014-09-12
  • Supported by:

    Project supported by the Young Teachers Program of Universities in Shanghai (No. yyy11015) and the National Natural Science Foundation of China (No. 21402121)

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 SN2'-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