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Total Synthesis of the Naturally Occurring Glycosylflavone Aciculatin
Chun-Hsu Yao1, Chi-Hui Tsai1, Jinq-Chyi Lee1
1Institute of Biotechnology and Pharmaceutical Research, National Health Research Institutes , 35 Keyan Road, Zhunan, Miaoli County 35053, Taiwan.
Abstract:
The new flavone-glycoside aciculatin (1), from Chrysopogon aciculatus, has been shown to have cytotoxic, anti-inflammatory, and antiarthritis activity. Further biological studies have been limited because of the limited availability of 1 from natural sources. Herein the first total synthesis of 1 in an overall yield of 8.3% is described. The synthesis involved the regio- and stereoselective glycosylation-Fries-type O-to-C rearrangement to construct the C-aryl glycosidic linkage, followed by a Baker-Venkataraman rearrangement and cyclodehydration to form the flavone scaffold.
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