Total Synthesis of the Naturally Occurring Glycosylflavone Aciculatin
| Autor: | Chun-Hsu Yao, Chi-Hui Tsai, Jinq-Chyi Lee |
|---|---|
| Rok vydání: | 2016 |
| Předmět: |
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 |
| Zdroj: | Journal of Natural Products. 79:1719-1723 |
| ISSN: | 1520-6025 0163-3864 |
| DOI: | 10.1021/acs.jnatprod.5b01051 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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