Bioactive Phytochemicals: Efficient Synthesis of Optically Active Substituted Flav-3-enes and Flav-3-en-3-o-R Derivatives
| Autor: | MC Achilonu, M. M. Sedibe, Karabo Shale |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2017 |
| Předmět: |
Antioxidant
Article Subject 010405 organic chemistry Chemistry medicine.medical_treatment General Chemistry 010402 general chemistry 01 natural sciences Chemical synthesis 0104 chemical sciences lcsh:Chemistry chemistry.chemical_compound lcsh:QD1-999 Acetylation Yield (chemistry) medicine Organic chemistry Moiety Stereoselectivity Methanol Trifluoromethanesulfonate |
| Zdroj: | Journal of Chemistry, Vol 2017 (2017) |
| ISSN: | 2090-9071 2090-9063 |
| Popis: | The structural core of flavene (2-phenyl-2H-chromene) is commonly found in plant flavonoids, which exhibit a wide range of biological activities and diverse pharmacological profiles (e.g., antioxidant and anticancer activities). Flavonoids have attracted significant interest in medicinal and synthetic chemistry. Substituted flav-3-ene 13 was exclusively synthesized by the stereoselective elimination of the O-mesyl moiety on C-3 of 5,7,3′,4′-tetramethoxyflavan-3-mesylate 12 with 1,8-diazabicyclo[5.4.0]undec-7-ene. The reaction of 5,7,3′,4′-tetramethoxyflavan-3-one 15 with ytterbium trifluoromethanesulfonate in methanol afforded a novel 3-O-substituted flav-3-ene derivative (3,5,7,3′,4′-pentamethoxyflav-3-ene) 17. The reduction of 4-(1,3,5-trihydroxybenzene)-5,7,3′,4′-tetra-O-benzylflavan-3-one 19b with hydrogen afforded a new compound: 3-hydroxy-4-(1,3,5-trihydroxybenzene)-5,7,3′,4′-tetrahydroxyflavan-3-en-3-ol 21 in good yield (95%), while the acetylation of 19a and 21 afforded the expected novel flav-3-en-3-acetoxy derivatives 20 (92%) and 22 (90%), respectively. |
| Databáze: | OpenAIRE |
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