Total syntheses of iso-, neuro- and phytoprostanes: new insight in lipid chemistry.
Isoprostanes (IsoPs) are a complex family of compounds produced, in vivo, from peroxidation of polyunsaturated fatty acids (AA, DHA, EPA, alpha-linolenic) via a free-radical-catalyzed mechanism. Carbocyclic annulations are extremely important reactions and the stereocontrolled intramolecular free-radical cyclization has emerged as a powerful tool for carbon-carbon bond formation in synthetic chemistry. The hex-5-enyl radical cyclization is the most well-known for the synthesis of cyclopentane rings. After a short review of the literature, concerning the total synthesis of isoprostanes and intermediates, we will present our own contributions on the preparation of chiral cyclopentane rings from glucose leading to new isoprostanes. This study allowed us to control the cyclization outcome to yield the all-syn and/or syn-anti-syn precursors which permit us to the total synthesis of a large set of iso-, neuro-, and phytoprostanes.
Durand
Thierry
T
UMR CNRS 5074, Faculté de Pharmacie, Université de Montpellier I, 15, Av. Charles Flahault. BP 14491, 34093 Montpellier Cedex 5, France. Thierry.Durand@univ-montp1.fr
Guy
Alexandre
A
Henry
Olivier
O
Roland
Arlène
A
Bernad
Stéphane
S
El Fangour
Siham
S
Vidal
Jean-Pierre
JP
Rossi
Jean-Claude
JC
D001095:Arachidonic Acids / Q000138:chemical synthesis*; D008055:Lipids / Q000737:chemistry*; D015394:Molecular Structure
D001095:Arachidonic Acids; D008055:Lipids