Total synthesis of 15-D2t- and 15-epi-15-E2t- isoprostanes

Abstract

(Figure Presented) The first total synthesis of 15-D2t- isoprostane is described. (-)-(9S,15S)-15-D2t-IsoP 1 and (+)-(11R,15R)15-epi-15-E2t-IsoP 2 have been obtained in 15 steps from orthogonally protected enantiopure bicycle 3. Key features include an easy introduction of die cis side chains via ozonolysis, a highly selective enzymatic chemical differentiation of a non-meso-1,5-diol, and the use of a common synthetic intermediate allowing a stereodivergent approach to the target molecules. © 2010 American Chemical Society.