1. Total Synthesis of the Naturally Occurring Glycosylflavone Aciculatin
- Author
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Chun-Hsu Yao, Chi-Hui Tsai, and Jinq-Chyi Lee
- Subjects
Glycosylation ,Stereochemistry ,Aciculatin ,Pharmaceutical Science ,Poaceae ,010402 general chemistry ,01 natural sciences ,Analytical Chemistry ,chemistry.chemical_compound ,Drug Discovery ,Organic chemistry ,Glycosides ,Flavonoids ,Pharmacology ,chemistry.chemical_classification ,Molecular Structure ,biology ,010405 organic chemistry ,Chrysopogon aciculatus ,Organic Chemistry ,Total synthesis ,Glycoside ,Glycosidic bond ,biology.organism_classification ,0104 chemical sciences ,Complementary and alternative medicine ,chemistry ,Yield (chemistry) ,Molecular Medicine ,Stereoselectivity - 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.
- Published
- 2016
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