The Piancatelli rearrangement of non-symmetrical furan-2,5dicarbinols for the synthesis of highly functionalized cyclopentenones
| Autor: | Le Goff, Géraldine, Cacheux, Fanny, Goff, Géraldine, Ouazzani, Jamal, Bignon, Jérôme, Retailleau, Pascal, Marinetti, Angela, Voituriez, Arnaud, Betzer, Jean-François |
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| Přispěvatelé: | Institut de Chimie des Substances Naturelles (ICSN), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC) |
| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
Cyclopentenone
010405 organic chemistry [CHIM.ORGA]Chemical Sciences/Organic chemistry Organic Chemistry 010402 general chemistry 01 natural sciences 0104 chemical sciences Catalysis Human tumor chemistry.chemical_compound chemistry Nucleophile Furan Organic chemistry Hydroxymethylfurfural Piancatelli rearrangement |
| Zdroj: | Organic Chemistry Frontiers Organic Chemistry Frontiers, Royal Society of Chemistry, 2021, ⟨10.1039/D1QO00268F⟩ |
| ISSN: | 2052-4129 |
| DOI: | 10.1039/D1QO00268F⟩ |
| Popis: | International audience; 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. |
| Databáze: | OpenAIRE |
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