Synthesis of the eight enantiomerically pure diastereomers of the 12-F(2)-isoprostanes

Syntheses of the eight enantiomerically pure diastereomers of the 12-F(2)-isoprostanes (4-11) are described. The key steps included rhodium-mediated intramolecular cyclopropanation and enzymatic resolution of the racemic diol 12.