title: Total syntheses of iso-, neuro- and phytoprostanes: new insight in lipid chemistry.
abstract: 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.
authors.affiliation: 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
authors.forename: Thierry
authors.initials: T
authors.lastname: Durand
authors.forename: Alexandre
authors.initials: A
authors.lastname: Guy
authors.forename: Olivier
authors.initials: O
authors.lastname: Henry
authors.forename: Arlène
authors.initials: A
authors.lastname: Roland
authors.forename: Stéphane
authors.initials: S
authors.lastname: Bernad
authors.forename: Siham
authors.initials: S
authors.lastname: El Fangour
authors.forename: Jean-Pierre
authors.initials: JP
authors.lastname: Vidal
authors.forename: Jean-Claude
authors.initials: JC
authors.lastname: Rossi
mesh_terms: D001095:Arachidonic Acids / Q000138:chemical synthesis*; D008055:Lipids / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: D001095:Arachidonic Acids; D008055:Lipids