- Syntheses stereoselectives de metabolites hydroxyles d'acides gras polyinsatures
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The E,Z dienol structure is characteristic of the basic structure of most of the polyunsaturated fatty acid metabolites.In this paper are described our results concerning a new approach towards molecules of this type.The key features of this strategy include: 1) the use of the, easily available, fumaraldehyde monodimethylacetal 4 as a key intermediate for the synthesis of such compounds in racemic form and 2) the use of the chiral sorbic acid tricarbonyl ion complex 8 as a resolving agent.The methodology allows then the synthesis of several fatty acid metabolites such as 4-hydroxy-2-nonenal 14, coriolic and tetranorcoriolic acid methyl esters 28 and 31, trienals 39 or 40, and the 12-hydroxy-5,8,10 heptadecatrienoic ester 41.Some of them have been tested as part of a program dealing with the interaction of blood platelets and eicosanoids; it gave new results concerning the influence of the absolute configuration at the carbon bearing the hydroxyl group and the stereochemistry of the diene.
- Montarby, Lucy de,Tourbah, Hiam,Gree, Rene
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p. 419 - 432
(2007/10/02)
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