A PRACTICAL SYNTHESIS OF (R)-(E)-4-HYDROXYALK-2-ENAL AND (S)-(E)-4-HYDROXYALK-2-ENAL, CYTOTOXIC PRODUCTS OF THE MICROSOMAL LIPID-PEROXIDATION

Authors
ALLEVI P ANASTASIA M CIUFFREDA P SANVITO AM
Citation
P. Allevi et al., A PRACTICAL SYNTHESIS OF (R)-(E)-4-HYDROXYALK-2-ENAL AND (S)-(E)-4-HYDROXYALK-2-ENAL, CYTOTOXIC PRODUCTS OF THE MICROSOMAL LIPID-PEROXIDATION, Tetrahedron : asymmetry, 5(5), 1994, pp. 927-934
Citations number
24
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
5
Issue
5
Year of publication
1994
Pages
927 - 934
Database
ISI
SICI code
0957-4166(1994)5:5<927:APSO(A>2.0.ZU;2-C
Abstract
The chemical synthesis of some (S)- and (R)-(E)-4-hydroxyalk-2-enals, important products of lipid peroxidation (LPO), has been carried out v ia enantiomerically pure 2-benzoyloxyaldehydes, chiral key intermediat es obtained from two diastereomeric diepoxides deriving from D-mannito l. These aldehydes were transformed into the final compounds by Wittig condensation with (formylmethylene)triphenylphosphorane and regenerat ion of the hydroxy group.