The chemical synthesis of some (S)- and (R)-(E)-4-hydroxyalk-2-enals, important products of lipid peroxidation (LPO), has been carried out via enantiomerically pure 2-benzoyloxyaldehydes, chiral key intermediates obtained from two diastereomeric diepoxides deriving from D-mannitol. These aldehydes were transformed into the final compounds by Wittig condensation with (formylmethylene)triphenylphosphorane and regeneration of the hydroxy group.
A PRACTICAL SYNTHESIS OF (R)-(E)-4-HYDROXYALK-2-ENAL AND (S)-(E)-4-HYDROXYALK-2-ENAL, CYTOTOXIC PRODUCTS OF THE MICROSOMAL LIPID-PEROXIDATION / P. ALLEVI, M. ANASTASIA, P. CIUFFREDA, A. SANVITO. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 5:5(1994), pp. 927-934. [10.1016/S0957-4166(00)86245-X]
A PRACTICAL SYNTHESIS OF (R)-(E)-4-HYDROXYALK-2-ENAL AND (S)-(E)-4-HYDROXYALK-2-ENAL, CYTOTOXIC PRODUCTS OF THE MICROSOMAL LIPID-PEROXIDATION
P. ALLEVIPrimo
;M. ANASTASIASecondo
;P. CIUFFREDAPenultimo
;
1994
Abstract
The chemical synthesis of some (S)- and (R)-(E)-4-hydroxyalk-2-enals, important products of lipid peroxidation (LPO), has been carried out via enantiomerically pure 2-benzoyloxyaldehydes, chiral key intermediates obtained from two diastereomeric diepoxides deriving from D-mannitol. These aldehydes were transformed into the final compounds by Wittig condensation with (formylmethylene)triphenylphosphorane and regeneration of the hydroxy group.
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