Synthesis and discovery of phytofurans: metabolites of α-linolenic acid peroxidation.
- Resource Type
- Article
- Authors
- Cuyamendous, C.; Leung, K. S.; Durand, T.; Lee, J. C.-Y.; Oger, C.; Galano, J.-M.
- Source
- Chemical Communications. 11/7/2015, Vol. 51 Issue 86, p15696-15699. 4p.
- Subject
- *FURANS synthesis
*LINOLENIC acids
*PEROXIDATION
*REARRANGEMENTS (Chemistry)
*TETRAHYDROFURAN
*LIQUID chromatography-mass spectrometry
*PLANT metabolites
- Language
- ISSN
- 1359-7345
Phytofurans are novel metabolites produced by non-enzymatic peroxidation of α-linolenic acid. An unprecedented Payne rearrangement-cyclization of a C2-symmetric bis-epoxide permitted construction of the core 3-hydroxy-2,5-disubstituted tetrahydrofuran. LC-MS/MS investigation provided evidence for the presence of phytofurans in nuts and seeds for the first time. [ABSTRACT FROM AUTHOR]