Synthesis of the eight enantiomerically pure diastereomers of the 12-F2-Isoprostanes

DF Taber, M Xu, JC Hartnett

Index: Taber, Douglass F.; Xu, Ming; Hartnett, John C. Journal of the American Chemical Society, 2002 , vol. 124, # 44 p. 13121 - 13126

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Citation Number: 47

Abstract

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. ... The isoprostanes (eg 1−4), a new family of prostaglandin-like compounds, were recently discovered to be produced in vivo in humans, independent of the cyclooxygenase enzymes, by free radical mediated oxidation of membrane-bound ...