Total Synthesis of Isoprostanes Derived from Adrenic Acid and EPA

Camille Oger (1) , Valérie Bultel-Poncé (1) , Alexandre Guy (1) , Thierry Durand (1) , Jean-Marie Galano (1)

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

Enantiomerically enriched F2-dihomo-isoprostanes and F3isoprostanes have been synthesized. Such compounds are derived from the action of reactive oxygen species on the phospholipid-bound polyunsaturated fatty acids (PUFA), adrenic acid and eicosapentaenoic acid, respectively. Of special interest are the F2-dihomo-isoprostanes because they could represent potential biomarkers for myelin damage as its main PUFA constituent is adrenic acid. Our strategy, based on a pivotal enantiomerically enriched intermediate, has allowed access to F2-dihomo-IsoP and both C5 epimers of 5-F3t-IsoP for the first time.

Mots clés: Biomarkers; Oxidation; Total synthesis; Natural products

Domaines: Chimie organique

Camille Oger, Valérie Bultel-Poncé, Alexandre Guy, Thierry Durand, Jean-Marie Galano. Total Synthesis of Isoprostanes Derived from Adrenic Acid and EPA. European Journal of Organic Chemistry, 2012, pp.2621-2634. ⟨10.1002/ejoc.201200070⟩. ⟨hal-00691200⟩