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Total Synthesis of Icaritin via Microwave-assistance Claisen Rearrangement

[ Vol. 11 , Issue. 9 ]


Van-Son Nguyen, Ling Shi, Yue Li and Qiu-An Wang   Pages 677 - 681 ( 5 )


The novel total synthesis of icaritin (1), naturally occurring with important bioactive 8-prenylflavonoid, was performed via a reaction sequence of 8 steps including Baker-Venkataraman reaction, chemoselective benzyl or methoxymethyl protection, dimethyldioxirane (DMDO) oxidation, O-prenylation, Claisen rearrangement and deprotection, starting from 2,4,6-trihydroxyacetophenone and 4-hydroxybenzoic acid in overall yields of 23%. The key step was Claisen rearrangement under microwave irradiation. MS, 1H and 13C NMR techniques have been used to confirm the structures of all synthetic compounds.


Icaritin, flavonoid, total synthesis, claisen rearrangement, microwave-assistance.


College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, P.R. China.

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