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

Fanny Cacheux (1) , Géraldine Le Goff (1) , Jamal Ouazzani (1) , Jérôme Bignon (1) , Pascal Retailleau (1) , Angela Marinetti (1) , Arnaud Voituriez (1) , Jean-François Betzer (1)

1 ICSN - Institut de Chimie des Substances Naturelles

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.

Domains: Organic chemistry

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