Stereocontrolled access to isoprostanes via a bicyclo[3.3.0]octene framework |
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Authors: | Oger Camille Brinkmann Yasmin Bouazzaoui Samira Durand Thierry Galano Jean-Marie |
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Institution: | 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. |
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Abstract: | We report a simple and highly stereocontrolled strategy toward the total synthesis of isoprostanes based on a bicyclic alpha,beta-epoxy ketone intermediate 6. Bicyclo3.3.0]octene scaffold permitted stereodirection of reagents allowing stereoselective epoxidation, diastereoselective ketone reduction, and regioselective epoxide opening otherwise not accessible with a simple cyclopentene framework. |
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