Tetrahedron letters

The first synthesis of Threo-and Erythro-(E)-4, 5-dihydroxydec-2-enals carbonyls related to the peroxidation of liver microsomal lipids

P Allevi, F Cajone, P Ciuffreda, M Anastasia

Index: Allevi, Pietro; Cajone, Francesco; Ciuffreda, Pierangela; Anastasia, Mario Tetrahedron Letters, 1995 , vol. 36, # 8 p. 1347 - 1350

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Citation Number: 7

Abstract

The first synthesis of threo and erythro (E)-4, 5-dihydroxydec-2-enals, aldehydes related to the lipid peroxidation is accomplished by reaction of α-benzoyloxheptanal with the Grignard reagent of 3, 3-diethoxy-1-propyne and lithium aluminum hydride reduction. Acetonization of the diol system allows a simple chromatographic separation of the diastereoisomers, the geometry of which was established by 1H and 13C NMR experiments and was confirmed ...