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

Yasmin Brinkmann (1) , Camille Oger (1) , Guy Alexandre (1) , Thierry Durand (1) , Jean-Marie Galano (1)

1 IBMM - Institut des Biomolécules Max Mousseron [Pôle Chimie Balard]

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.

Mots clés: 15-D2-IsoP; 15-E2t-IsoP; total synthesis; selective enzymatic chemical differentiation of a non-meso-1; 5-diols

Domaines: Chimie organique

Yasmin Brinkmann, Camille Oger, Guy Alexandre, Thierry Durand, Jean-Marie Galano. Total Synthesis of 15-D2t- and 15-epi-15-E2t-Isoprostanes. Journal of Organic Chemistry, 2010, 75 (7), pp.2411-2414. ⟨10.1021/jo1000274⟩. ⟨hal-00466853⟩