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Total Synthesis of 15-D2t- and 15-epi-15-E2t-Isoprostanes

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journal contribution
posted on 02.04.2010, 00:00 by Yasmin Brinkmann, Camille Oger, Alexandre Guy, Thierry Durand, Jean-Marie Galano
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 the 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.