The Piancatelli rearrangement of non-symmetrical furan-2,5dicarbinols for the synthesis of highly functionalized cyclopentenones - Archive ouverte HAL Access content directly
Journal Articles Organic Chemistry Frontiers Year : 2021

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

(1) , (1) , (1) , (1) , (1) , (1) , (1) , (1)
1

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.
Fichier principal
Vignette du fichier
OCF 2021-03-15 Piancatelli - OCF - HAL.pdf (991.47 Ko) Télécharger le fichier
Origin : Files produced by the author(s)

Dates and versions

hal-03215511 , version 1 (03-05-2021)

Identifiers

Cite

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⟩
115 View
113 Download

Altmetric

Share

Gmail Facebook Twitter LinkedIn More