Journal of Organic Chemistry p. 2411 - 2414 (2010)
Update date:2022-08-04
Topics:
Brinkmann, Yasmin
Oger, Camille
Guy, Alexandre
Durand, Thierry
Galano, Jean-Marie
(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.
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