THE ISOPROSTANES, A NEW CLASS OF NATURAL-PRODUCTS - SYNTHESIS AND BIOSYNTHESIS

A new class of natural products called isoprostanes are formed in huma ns as a result of non-enzymatic free-radical-catalyzed lipid peroxidat ion. Isoprostanes possess biological activity and can be used as an in dex of free-radical lipid peroxidation and as a marker of oxidative st ress. We report here a new and general synthetic methodology for the s yntheses of isoprostanes, using the four key lactones which are constr ucted from D-and L-glucose by a thionocarbonate-mediated radical cycli zation reaction. These lactones possess the required stereochemistry a nd the right functional groups for the syntheses of isoprostanes.