Chinese Journal of Organic Chemistry >
Chemistry and Biology of Bakuchiol
Received date: 2014-08-14
Revised date: 2014-09-09
Online 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
Huang Shahua , Huang Mengyuan , Jia Xueshun , Hong Ran . Chemistry and Biology of Bakuchiol[J]. Chinese Journal of Organic Chemistry, 2014 , 34(12) : 2412 -2423 . DOI: 10.6023/cjoc201408015
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