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Bioactive Phytochemicals: Efficient Synthesis of Optically Active Substituted Flav-3-enes and Flav-3-en-3-o-R Derivatives
Joint Authors
Achilonu, Matthew C.
Sedibe, Moosa Mahmood
Shale, Karabo
Source
Issue
Vol. 2017, Issue 2017 (31 Dec. 2017), pp.1-11, 11 p.
Publisher
Hindawi Publishing Corporation
Publication Date
2017-05-18
Country of Publication
Egypt
No. of Pages
11
Main Subjects
Abstract EN
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.
American Psychological Association (APA)
Achilonu, Matthew C.& Sedibe, Moosa Mahmood& Shale, Karabo. 2017. Bioactive Phytochemicals: Efficient Synthesis of Optically Active Substituted Flav-3-enes and Flav-3-en-3-o-R Derivatives. Journal of Chemistry،Vol. 2017, no. 2017, pp.1-11.
https://search.emarefa.net/detail/BIM-1171785
Modern Language Association (MLA)
Achilonu, Matthew C.…[et al.]. Bioactive Phytochemicals: Efficient Synthesis of Optically Active Substituted Flav-3-enes and Flav-3-en-3-o-R Derivatives. Journal of Chemistry No. 2017 (2017), pp.1-11.
https://search.emarefa.net/detail/BIM-1171785
American Medical Association (AMA)
Achilonu, Matthew C.& Sedibe, Moosa Mahmood& Shale, Karabo. Bioactive Phytochemicals: Efficient Synthesis of Optically Active Substituted Flav-3-enes and Flav-3-en-3-o-R Derivatives. Journal of Chemistry. 2017. Vol. 2017, no. 2017, pp.1-11.
https://search.emarefa.net/detail/BIM-1171785
Data Type
Journal Articles
Language
English
Notes
Includes bibliographical references
Record ID
BIM-1171785