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

Jean-Marc Dillenschneider 1 Laurent Dufossé 2 Mireille Fouillaud 2 Nuthathai Sutthiwong 2, 3 Roger Labia 4, 1 Alain Valla 4, 1
1 LCSN - Laboratoire de Chimie des Substances Naturelles
2 LCSNSA - Laboratoire de Chimie des Substances Naturelles et des Sciences des Aliments
3 TISTR - Thailand Institute of Scientific and Technological Research
4 Chimie et biologie des substances naturelles
Abstract : 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.
Document type :
Journal articles
Complete list of metadatas

Cited literature [4 references]  Display  Hide  Download
https://hal.univ-reunion.fr/hal-01188091
Contributor : Claire Tessier <>
Submitted on : Saturday, November 19, 2016 - 8:48:11 AM
Last modification on : Monday, September 2, 2019 - 9:43:01 AM
Long-term archiving on : Monday, March 27, 2017 - 9:06:08 AM

File

Dillenschneider2016B_hal.pdf
Files produced by the author(s)

Identifiers

Collections

CNRS | LCSNSA | UNIV-REUNION | PAPANGUE | FST-REUNION

Citation

Jean-Marc Dillenschneider, Laurent Dufossé, Mireille Fouillaud, Nuthathai Sutthiwong, Roger Labia, et al.. Two-step Synthesis of New γ-Lactones via Cyclization of 7-Chloro-2-(methoxycarbonyl)-4-6-dimethylocta-(2E,4E,6E)-trienoic acid. Journal of Heterocyclic Chemistry, Wiley, 2016, 53 (5), pp.1439-1442. ⟨10.1002/jhet.2444⟩. ⟨hal-01188091⟩

Export

BibTeX TEI DC DCterms EndNote

Share

Metrics

Record views

283

Files downloads

162

Contact

CCSD