Total Synthesis of the Naturally Occurring Glycosylflavone Aciculatin.
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.
Institute of Biotechnology and Pharmaceutical Research, National Health Research Institutes , 35 Keyan Road, Zhunan, Miaoli County 35053, Taiwan.
Chun-Hsu
CH
Yao
Institute of Biotechnology and Pharmaceutical Research, National Health Research Institutes , 35 Keyan Road, Zhunan, Miaoli County 35053, Taiwan.
Chi-Hui
CH
Tsai
Institute of Biotechnology and Pharmaceutical Research, National Health Research Institutes , 35 Keyan Road, Zhunan, Miaoli County 35053, Taiwan.
Jinq-Chyi
JC
Lee
D005419:Flavonoids / Q000138:chemical synthesis* / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D015394:Molecular Structure; D006109:Poaceae / Q000737:chemistry*
D005419:Flavonoids; D006027:Glycosides; C074400:aciculatin