118908-15-9Relevant articles and documents
Asymmetric synthesis of γ-hydroxy α, β-unsaturated amides via an AD-elimination process; synthesis of (+)-Coriolic acid
Bennani, Youssef L.,Barry Sharpless
, p. 2083 - 2086 (1993)
An efficient, asymmetric synthetic route to γ-hydroxy α,β-imsaturated ketone and/or aldehyde equivalents is described. Thus, 3,4-dihydroxy N-methoxy-N-methyl amides are treated in a one pot process with thionyl chloride followed by DBU to give the corresponding γ-hydroxy α,β-unsaturated amides in good yields. Based on this methodology, a short sequence leading to natural (+)-Coroilic acid is presented.
Syntheses stereoselectives de metabolites hydroxyles d'acides gras polyinsatures
Montarby, Lucy de,Tourbah, Hiam,Gree, Rene
, p. 419 - 432 (2007/10/02)
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.
The total syntheses of several 8,15 dihydroxy arachidonic acid derivatives (8,15, LTB's)
Fitzsimmons,Rokach
, p. 3043 - 3046 (2007/10/02)
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