76745-20-5Relevant academic research and scientific papers
BIFUNCTIONAL CHIRAL SYNTHONS VIA MICROBIOLOGICAL METHODS. 2. OPTICALLY-ACTIVE α-HYDROXY ALDEHYDES.
Takaishi, Yoshihisa,Yang, Yuh-Lin,DiTullio, Dennis,Sih, Charles J.
, p. 5489 - 5492 (1982)
A versatile chemical-microbiological approach has been developed for the preparation of chiral α-hydroxy aldehydes via stereoselective reduction of the corresponding α-keto thioacetals or via optical resolution of the racemic α-acetoxy esters.
12-Oxo-LTB4, a key pivotal intermediate in LTB4 metabolism
Khanapure,Manna,Rokach,Murphy,Wheelan,Powell
, p. 1806 - 1813 (2007/10/02)
The first total synthesis of the very unstable and elusive biochemical intermediate 5(S)-hydroxy-12-oxo-6(Z),8(E),10(E),14(Z)-eicosatetraenoic acid (12-oxo-LTB4) (2) has been accomplished. Incubation of the synthetic 12-oxo-LTB4 (2) with human keratinocytes produced 5(S),12-dihydroxy-6-glutathionyl-7(E),9(E),14(Z)-eicosatrienoic acid (c-LTB3) and 5(S),12-dihydroxy-6-cysteinylglycyl-7(E),9(E),14(Z)-eicosatrienoic acid (d-LTB3), two new intriguing mediators which have been identified recently during the incubations of LTB4 with keratinocytes. We have also confirmed the identity of 12-oxo-LTB4 prepared from porcine leukocytes by comparison with the synthetic material and identified the formation in these incubates of the 6-trans-isomer of 12-oxo-LTB4.
Microbial approach to chiral 2-thiazolyl γ- and δ lactones
Fantin,Fogagnolo,Medici,Pedrini,Poli,Gardini,Guerzoni
, p. 107 - 114 (2007/10/02)
The synthesis of chiral 2-thiazolyl γ- and δ-lactones 6 and 7 via microbial reduction of the appropriate keto esters to the homochiral hydroxy esters followed by chemical lactonization is described. Some attempts of enzymatic lactonization of the racemic
A PRACTICAL METHOD FOR THE PRODUCTION OF METHYL 5(S)-BENZOYLOXY-5-FORMYLPENTANOATE - A KEY INTERMEDIATE IN THE SYNTHESIS OF LEUKOTRIENE B4
Kornilov, A. M.,Furmanova, M. V.,Sorochinskii, A. E.,Kukhar', V. P.
, p. 1067 - 1069 (2007/10/02)
Catalytic epoxidation of methyl 7-hydroxy-5(E)-heptenoate by the Sharpless method gave optically pure (5R,6R)-methyl 5,6-epoxy-7-hydroxyheptanoate, in which regioselective opening of the epoxide ring by benzoic acid with the assistance of titanium tetrais
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.
A Practical Preparation of α-Hydroxy and α,β-Dihydroxy Aldehydes, Useful Intermediates for the Synthesis of Arachidonic Acid Metabolites, starting with D-Glyceraldehyde Acetonide
Okamoto, Sentaro,Shimazaki, Toshiyuki,Kitano, Yasunori,Kobayashi, Yuichi,Sato, Fumie
, p. 1352 - 1355 (2007/10/02)
Optically active α-hydroxy and α,β-dihydroxy aldehydes, useful intermediates for synthesis of lipoxygenase metabolites of arachidonic acid, are synthesized highly diastereoselectively starting with readily available D-glyceraldehyde acetonide.
OPTICALLY ACTIVE PROPARGYLIC ALCOHOLS FROM D-XYLOSE USEFUL PRECURSORS FOR LTB4 SYNTHESIS
Pianetti, P.,Rollin, P.,Pougny, J. R.
, p. 5853 - 5856 (2007/10/02)
Using D-Xylose as a source of chirality at C-5 and C-12 in LTB4, an efficient synthesis of the optically active propargylic alcohols A and B, chiral precursors for the LTB4 synthesis, has been achieved.
Synthesis of (3S,4R)-Eldanolide and (5S,12R)-Leukotriene-B4 through Photolysis of Optically Active Hydroxy-7,7-dimethylbicycloheptanones
Davies, H. Geoff,Roberts, Stanley M.,Wakefield, Basil J.,Winders, John A.
, p. 1166 - 1168 (2007/10/02)
Photoisomerisation of 3-hydroxy-7,7-dimethylbicycloheptan-6-ones is the key step in a new route to the pheromone eldanolide while leukotriene-B4 is available through a photolytic retro reaction of 2-hydroxy-7,7-dimethylbicycloheptan-6-ones.
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.
A STEREOCONTROLLED AND EFFECTIVE SYNTHESIS OF LEUKOTRIENE B (1).
Corey, E. J.,Marfat, Anthony,Munroe, John,Kim, Kwan Soo,Hopkins, Paul B.,Brion, Francis
, p. 1077 - 1080 (2007/10/02)
An efficient synthesis of leukotriene B (1) is reported which renders this important substance accessible in quantity.The process is convergent and includes a novel method for stereospecific generation of the conjugated triene unit.
