Stereocontrolled access to isoprostanes via a bicyclo[3.3.0]octene framework.
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.
Oger
Camille
C
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.
Brinkmann
Yasmin
Y
Bouazzaoui
Samira
S
Durand
Thierry
T
Galano
Jean-Marie
JM
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D028421:Isoprostanes / Q000737:chemistry*; D015394:Molecular Structure; D009795:Octanes / Q000737:chemistry*; D013237:Stereoisomerism
D019086:Bridged Bicyclo Compounds, Heterocyclic; D028421:Isoprostanes; D009795:Octanes; C026728:octane