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Issue 11, 2021
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The Piancatelli rearrangement of non-symmetrical furan-2,5-dicarbinols for the synthesis of highly functionalized cyclopentenones

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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.

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

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Article information


Submitted
15 Feb 2021
Accepted
12 Mar 2021
First published
16 Mar 2021

Org. Chem. Front., 2021,8, 2449-2455
Article type
Research Article

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

F. Cacheux, G. Le Goff, J. Ouazzani, J. Bignon, P. Retailleau, A. Marinetti, A. Voituriez and J. Betzer, Org. Chem. Front., 2021, 8, 2449 DOI: 10.1039/D1QO00268F

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