Generic placeholder image

Letters in Organic Chemistry


ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Total Synthesis of Icaritin via Microwave-assistance Claisen Rearrangement

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

Volume 11, Issue 9, 2014

Page: [677 - 681] Pages: 5

DOI: 10.2174/157017861109140903103927

Price: $65


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.

Graphical Abstract

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy