Total Synthesis of Icaritin via Microwave-assistance Claisen Rearrangement

Author(s): Van-Son Nguyen, Ling Shi, Yue Li, Qiu-An Wang.

Journal Name: Letters in Organic Chemistry

Volume 11 , Issue 9 , 2014

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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.

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Article Details

VOLUME: 11
ISSUE: 9
Year: 2014
Page: [677 - 681]
Pages: 5
DOI: 10.2174/157017861109140903103927
Price: $58

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