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

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, 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.
Document type :
Journal articles
Complete list of metadatas

Cited literature [7 references]  Display  Hide  Download
https://hal.univ-reunion.fr/hal-01188092
Contributor : Claire Tessier <>
Submitted on : Saturday, November 19, 2016 - 8:39:09 AM
Last modification on : Monday, September 2, 2019 - 9:43:01 AM
Long-term archiving on: Tuesday, March 21, 2017 - 12:45:49 PM

File

Dillenschneider2016_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.. Novel π2s+π2a Electrocyclization of Triethylenic-Malonic Acids Exemplified for a One-Pot Synthesis of New γ-Dilactones cis-Fused with a Cyclopentene. Journal of Heterocyclic Chemistry, Wiley, 2016, 53 (4), pp.1017-1021. ⟨10.1002/jhet.2419⟩. ⟨hal-01188092⟩

Export

BibTeX TEI DC DCterms EndNote

Share

Metrics

Record views

202

Files downloads

138

Contact

CCSD