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Stereocontrolled Access to Isoprostanes via a Bicyclo[3.3.0]octene Framework

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journal contribution
posted on 06.11.2008 by Camille Oger, Yasmin Brinkmann, Samira Bouazzaoui, Thierry Durand, Jean-Marie Galano
We report a simple and highly stereocontrolled strategy toward the total synthesis of isoprostanes based on a bicyclic α,β-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.