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The Piancatelli rearrangement of non-symmetrical furan-2,5dicarbinols for the synthesis of highly functionalized cyclopentenones

Abstract : Substituted and non-symmetrical furan-2,5-dicarbinols were readily prepared from hydroxymethylfurfural (HMF), a renewable raw material from biomass. The Piancatelli rearrangement of these furan-2,5-dicarbinols, catalyzed by DyCl3 and under microwave activation, affords 5-substituted-4-hydroxymethyl-4-hydroxycyclopentenones in a regio-and diastereoselective manner. This methodology can be extended to aza-Piancatelli type reactions by using nitrogen nucleophiles, to furnish the corresponding aminocyclopentenone derivatives. These synthetized bis-hydroxylated cyclopentenone derivatives exhibited significant cytotoxicity against eight human tumor cell lines.
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https://hal-universite-paris-saclay.archives-ouvertes.fr/hal-03215511
Contributor : Jean-Francois Betzer Connect in order to contact the contributor
Submitted on : Monday, May 3, 2021 - 1:31:57 PM
Last modification on : Saturday, July 3, 2021 - 12:25:21 AM
Long-term archiving on: : Wednesday, August 4, 2021 - 7:05:58 PM

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Géraldine Le Goff, Fanny Cacheux, Géraldine Goff, Jamal Ouazzani, Jérôme Bignon, et al.. The Piancatelli rearrangement of non-symmetrical furan-2,5dicarbinols for the synthesis of highly functionalized cyclopentenones. Organic Chemistry Frontiers, Royal Society of Chemistry, 2021, ⟨10.1039/D1QO00268F⟩. ⟨hal-03215511⟩

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