100428-42-0Relevant articles and documents
New C3-synthons for the synthesis of natural products: (R)-glycidaldehyde diethyl dithioacetal and (R)-glycidaldehyde dimethyl acetal
Bestmann,Pecher,Riemer
, p. 731 - 734 (2007/10/02)
The glycidaldehyde acetals (R)-1,1-bis(ethylthio)-2,3-epoxypropane (5) and (R)-2,3-epoxy-1,1-dimethoxypropane (9) were obtained from (R)-2,3-O-isopropylideneglyceraldehyde [(4R)-2,2-dimethyl-1,3-dioxolane-4-carboxaldehyde] based on D-mannitol. The applica
Total Synthesis of Leukotriene B44> and Homo-LTB4 from D-Mannitol
Merrer, Yves Le,Gravier-Pelletier, Christine,Micas-Languin, Dominique,Mestre, Francoise,Dureault, Annie,Depezay, Jean-Claude
, p. 2409 - 2416 (2007/10/02)
A convergent total synthesis of leukotriene B4 and its homo analogue has been carried out via enantiomerically pure α-hydroxy aldehydes, chiral key intermediates obtained from D-mannitol and connected at a four carbon atom interval by Wittig re
Preparation d'α-hydroxyesters et d'α-hydroxyaldehydes enantiomeriquement purs. Application a la synthese enantiospecifique de la pheromone sexuelle de la cochenille Pseudococcus comstocki
Larcheveque, Marc,Petit, Yves
, p. 130 - 139 (2007/10/02)
Enantiomerically pure glycidic esters may be obtained in good yields by nitrous deamination of (S) or (R) serine; 2-bromo-3-hydroxy propionic acid is obtained and cyclized with alcoholic potash to give potassium glycidate; by reacting this salt with a sulfate, a primary iodide or an active bromide in acetonitrile in the presence of 18-crown-6, various glycidic esters were prepared.The ethyl glycidate reacts with lithiocuprates (alkyl or vinyl) but also with magnesiocuprates to afford a totally regiospecific reaction with the exclusive formation of α-hydroxyesters.The reaction is also possible with acetylides but it is necessary to use aluminium acetylides.With organolithium compounds reaction with the ester function of methyl glycidate occurs, leading to the formation of α-epoxyketones.The reduction of α-hydroxyesters (as protected form) with DIBAL-H at -70 deg C affords the corresponding α-hydroxyaldehydes in nearly quantitative yields.These reactions were applied to the synthesis of (R)-(+)-2,6-dimethyl-1,5-heptadien-3-ol acetate, the sex pheromone of the Comstock Mealybug, Pseudococcus comstocki.
A SIMPLE PREPARATION OF R OR S GLYCIDIC ESTERS; APPLICATION TO THE SYNTHESIS OF ENANTIOMERICALLY PURE α-HYDROXYESTERS
Larcheveque, Marc,Petit, Yves
, p. 1993 - 1996 (2007/10/02)
The simple preparation of enantiomerically pure α-hydroxyesters by the regioselective reaction of lithio and magnesiocuprates with glycidic esters 3 or 3' readily available from serine is described.
A Chemoenzymatic Synthesis of Leukotriene B4
Han, Chao-Qi,DiTullio, Dennis,Wang, Yi-Fong,Sih, Charles J.
, p. 1253 - 1258 (2007/10/02)
A total synthesis of leukotriene B4 (1) is accomplished by the assembly of the key chirons 2 and 3, which are prepared via enzymatic methods.
NON-CARBOHYDRATE BASED SYNTHESIS OF NATURAL LTB4
Fuganti, Claudio,Servi, Stefano,Zirotti, Carlo
, p. 5285 - 5288 (2007/10/02)
The synthesis of the C6(2S) and C10(2R) aldehydes (1) and (2), intermediates in reported syntheses of LTB4 (3), from the C4 aldehyde (4) throgh the alcohols (5) and (9) is described.
SIMPLE EFFICIENT SYNTHESIS OF LTB4 AND 12-epi-LTB4
Zamboni, Robert,Rokach, Joshua
, p. 2631 - 2634 (2007/10/02)
Using L- and D-arabinose respectively as the source of chirality at C-12 in LTB4, efficient new syntheses of LTB4 and 12-epi-LTB4 have been realized.
