The preparation of ketone 10 is described. Oxidation of 10 to the sulfoxide followed by sigmatropic rearrangement gave not the expected 15-D 2c -isoprostane ethyl ester ( 4 ), but the trans diastereomer 11 . A 13 C NMR method for establishment of the relative configuration of the cyclopentane rings of the isoprostanes and prostaglandins is also reported.
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Taber et al. (1998) studied this question.
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