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Stereocontrolled access to isoprostanes via a bicyclo[3.3.0]octene framework. 2008

Camille Oger, and Yasmin Brinkmann, and Samira Bouazzaoui, and Thierry Durand, and Jean-Marie Galano
Institut des Biomolécules Max Mousseron, IBMM, UMR CNRS 5247, Université Montpellier I, Faculté de Pharmacie, 15. Av. Ch. Flahault, F-34093 Montpellier cedex 05, France.

We report a simple and highly stereocontrolled strategy toward the total synthesis of isoprostanes based on a bicyclic alpha,beta-epoxy ketone intermediate 6. Bicyclo[3.3.0]octene scaffold permitted stereodirection of reagents allowing stereoselective epoxidation, diastereoselective ketone reduction, and regioselective epoxide opening otherwise not accessible with a simple cyclopentene framework.

UI MeSH Term Description Entries
D009795 Octanes Eight-carbon saturated hydrocarbon group of the methane series. Include isomers and derivatives. Isooctanes
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular
D019086 Bridged Bicyclo Compounds, Heterocyclic Heterocyclic compounds that contain two rings that share two non-adjacent atoms in common. Bicyclo Compounds, Heterocyclic,Heterocyclic Cpds, Bicyclic,Bicyclic Heterocyclic Compounds,Heterocyclic Bicyclo Compounds,Bicyclic Heterocyclic Cpds,Heterocyclic Compounds, Bicyclic
D028421 Isoprostanes A series of prostaglandin-like compounds that are produced by the attack of free-radical species on unsaturated fatty acids, especially ARACHIDONIC ACID, of cellular MEMBRANES. Once cleaved from the lipid membrane by the action of phospholipases they can circulate into various bodily fluids and eventually be excreted. Although these compounds resemble enzymatically synthesized prostaglandins their stereoisometric arrangement is usually different than the "naturally occurring" compounds. Isoprostane

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