Abstract
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 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 mols.