Novel π2s+π2a Electrocyclization of Triethylenic-Malonic Acids Exemplified for a One-Pot Synthesis of New γ-Dilactones cis-Fused with a Cyclopentene

Autor: Dillenschneider, Jean-Marc, Dufossé, Laurent, Fouillaud, Mireille, Sutthiwong, Nuthathai, Labia, Roger, Valla, Alain
Přispěvatelé: Molécules de Communication et Adaptation des Micro-organismes (MCAM), Muséum national d'Histoire naturelle (MNHN)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Chimie des Substances Naturelles et des Sciences des Aliments (LCSNSA), Université de La Réunion (UR), Thailand Institute of Scientific and Technological Research (TISTR), Thailand Institute of Scientific and Technological Research, Chimie et biologie des substances naturelles, Centre National de la Recherche Scientifique (CNRS), Tessier, Claire
Jazyk: angličtina
Rok vydání: 2016
Předmět:
Zdroj: Journal of Heterocyclic Chemistry
Journal of Heterocyclic Chemistry, Wiley, 2016, 53 (4), pp.1017-1021. ⟨10.1002/jhet.2419⟩
Journal of Heterocyclic Chemistry, 2016, 53 (4), pp.1017-1021. ⟨10.1002/jhet.2419⟩
ISSN: 0022-152X
1943-5193
DOI: 10.1002/jhet.2419⟩
Popis: International audience; A new, easy and rapid synthesis of γ-dilactones is cis-fused with a cyclopentenic ring via cyclization of 7-chlorotriethylenic-malonic acids. The key step implicates an intramolecular cyclization to a cyclopentenyl cation, according to an electrocyclic π2s + π2a conrotatory process. This cyclopentenyl cation led to unstable γ-lactones intermediates that are rearrange to more stable isomers. δ-lactones (6Z and 6E-(3-chlorobut-2-en-2-yl)-5-methyl-3,6-dihydro-2H-pyran-2-one) were obtained as secondary products. Mechanistic pathways were considered. The structures of the newly synthesized compounds were established by elemental and spectral data.
Databáze: OpenAIRE
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