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Total Synthesis of Icaritin via Microwave-assistance Claisen Rearrangement

[ Vol. 11 , Issue. 9 ]

Author(s):

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

Abstract:


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.

Keywords:

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

Affiliation:

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

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