THE FIRST SYNTHESIS OF THREO-(E)-4,5-DIHYDROXYDEC-2-ENAL AND ERYTHRO-(E)-4,5-DIHYDROXYDEC-2-ENAL CARBONYLS RELATED TO THE PEROXIDATION OF LIVER MICROSOMAL LIPIDS

被引：10

作者：

ALLEVI, P ^{[1
]}

CAJONE, F ^{[1
]}

CIUFFREDA, P ^{[1
]}

ANASTASIA, M ^{[1
]}

机构：

[1] UNIV MILAN,IST PATOL GEN,I-20133 MILAN,ITALY

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 08期

关键词：

D O I：

10.1016/0040-4039(94)02474-P

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first synthesis of three and erythro (E)-4,5-dihydroxydec-2-enals, aldehydes related to the lipid peroxidation is accomplished by reaction of alpha-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 H-1 and C-13 NMR experiments and was confirmed by an independent synthesis of (E,4R,5R)-4,5-O-isopropylidene-4,5-dihydroxydec-2-enal from D-mannitol.

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页码：1347 / 1350

页数：4

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