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Efficient Piancatelli rearrangement of HMF derivatives under microwave activation or subcritical water conditions to produce functionalized hydroxylated cyclopentenones. Efficient Piancatelli rearrangement of HMF derivatives under microwave activation or subcritical water conditions to produce functionalized hydroxylated cyclopentenones: The HMF was used to prepare precursors for Piancatelli rearrangement. These reactions performed under microwave activation or subcritical water conditions provide functionalized cyclopentenones, which exhibit antimicrobial activity.

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Youssef-Saliba, Sparta | Mayet, Clémentine | Elslande, Elsa Van | Le Goff, Géraldine | Betzer, Jean-François

Edité par CCSD ; Royal Society of Chemistry -

International audience. HMF (5-hydroxymethylfurfural), a renewable raw material from biomass, was used as starting material to provide 5-aryl-4-hydroxymethyl-4-hydroxycyclopentenones with functionalized aryl groups. In a first time, arylic substituents were added to the aldehyde moiety of HMF under rhodium- or palladium-catalyzed 1,2-addition of arylboronic acids, in mild conditions to respect the very sensitive HMF reactivity. In a second time, these non-symmetrical furan-2,5-dicarbinols, through Piancantelli rearrangement, provided the desired cyclopentenones under microwave activation or subcritical water conditions (100 °C and 100 bars) using the Zippertex technology, in regio- and diastereoselective manner. These synthetized bis-hydroxylated cyclopentenone derivatives exhibited significant antimicrobial activities against gram-positive bacteria Micrococcus luteus, Bacillus subtilis and gram-negative bacteria Echerichia coli.

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