Preparation of Synthetic and Natural Derivatives of Flavonoids Using Suzuki–Miyaura Cross-Coupling Reaction |
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| Authors: | Martina Hurtov David Biedermann Zuzana Osifov Josef Cva
ka Kate&#x;ina Valentov Vladimír K&#x;en |
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| Institution: | 1.Laboratory of Biotransformation, Institute of Microbiology of the Czech Academy of Sciences, Vídeňská 1083, CZ-14220 Prague, Czech Republic; (M.H.); (D.B.); (K.V.);2.Faculty of Food and Biochemical Technology, University of Chemistry and Technology Prague, Technická 5, CZ-16628 Prague, Czech Republic;3.Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Flemingovo nám. 542/2, CZ-16000 Prague, Czech Republic; (Z.O.); (J.C.) |
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| Abstract: | Herein, we report the use of the Suzuki–Miyaura cross-coupling reaction for the preparation of a library of synthetic derivatives of flavonoids for biological activity assays. We have investigated the reactivity of halogenated flavonoids with aryl boronates and with boronyl flavonoids. This reaction was used to prepare new synthetic derivatives of flavonoids substituted at C-8 with aryl, heteroaryl, alkyl, and boronate substituents. The formation of flavonoid boronate enabled a cross-coupling reaction with halogenated flavones yielding biflavonoids connected at C-8. This method was used for the preparation of natural compounds including C-8 prenylated compounds, such as sinoflavonoid NB. Flavonoid boronates were used for the preparation of rare C-8 hydroxyflavonoids (natural flavonoids gossypetin and hypolaetin). A series of previously unknown derivatives of quercetin and luteolin were prepared and fully characterized. |
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| Keywords: | flavonoids Suzuki– Miyaura cross-coupling reaction prenylation borylation |
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