A Synthetic Approach to 15-D_2c-Isoprostane Ethyl Ester

Abstract

The preparation of ketone 10 is described. Oxidation of 10 to the sulfoxide followed by sigmatropic rearrangement gave not the expected 15-D2c-isoprostane ethyl ester (4), but the trans diastereomer 11. A 13C NMR method for establishment of the relative configuration of the cyclopentane rings of the isoprostanes and prostaglandins is also reported