Two-step Synthesis of New γ-Lactones via Cyclization of 7-Chloro-2-(methoxycarbonyl)-4-6-dimethylocta-(2E,4E,6E)-trienoic acid

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 (5), pp.1439-1442. ⟨10.1002/jhet.2444⟩
Journal of Heterocyclic Chemistry, 2016, 53 (5), pp.1439-1442. ⟨10.1002/jhet.2444⟩
ISSN: 0022-152X
1943-5193
DOI: 10.1002/jhet.2444⟩
Popis: International audience; A new rapid synthesis of γ-lactones, cis fused with a cyclopentenic ring by thermal cyclization of 7-chloro-2-(methoxycarbonyl)-4-6-dimethylocta-7-phenyl (or methyl) (2E,4E,6E)-trienoic acids was reported. The key step implicates an intramolecular cyclization to a cyclopentenyl cation, according to an electrocyclic π2s + π2a conrotatory process, published in a recent paper (from the corresponding diacids). We have investigated the thermal behavior of the corresponding half-esters since; if the cyclization obeys to the proposed mechanism, the diacids, half-esters must also cyclize in a similar manner. Saponification of these led to γ-dilactones via intermediary cyclopropanes. Mechanistic pathways were investigated.
Databáze: OpenAIRE
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