502470-95-3Relevant academic research and scientific papers
Copper-Catalyzed Asymmetric Conjugate Addition of Dimethylzinc to Acyl-N-methylimidazole Michael Acceptors: Scope, Limitations and Iterative Reactions
Drissi-Amraoui, Sammy,Schmid, Thibault E.,Lauberteaux, Jimmy,Crévisy, Christophe,Baslé, Olivier,de Figueiredo, Renata Marcia,Halbert, Stéphanie,Gérard, Hélène,Mauduit, Marc,Campagne, Jean-Marc
, p. 2519 - 2540 (2016)
An efficient copper-catalyzed enantioselective conjugate addition of dimethylzinc to unsaturated 2-acyl-N-methylimidazoles has been achieved using a chiral bidentate hydroxyalkyl-NHC ligand. The reactions proceed with excellent regioselectivity (1,4 vs. 1,6 and 1,8) in extended conjugated systems to afford the 1,4-adducts in high enantioselectivities. This regioselectivity could be ascertained by DFT studies highlighting the crucial role of the imidazole ring. Thanks to the development of efficient protocols to regenerate the unsaturated 2-acyl-N-methylimidazole moiety, an iterative process has been developed ultimately leading to 3,5,7 all-syn or anti-anti polydeoxypropionate stereodiads. (Figure presented.).
Stereoselective synthesis of dienyl-carboxylate building blocks: Formal synthesis of inthomycin C
Souris, Caroline,Frebault, Frederic,Patel, Ashay,Audisio, Davide,Houk,Maulide, Nuno
, p. 3242 - 3245 (2013/07/26)
A direct synthesis of stereodefined halodienes is reported. Those key building blocks enable a concise access to polyenic products, as demonstrated in a modular synthesis of Inthomycin C.
Potent and selective fluoroketone inhibitors of group VIA calcium-independent phospholipase A2
Kokotos, George,Hsu, Yuan-Hao,Burke, John E.,Baskakis, Constantinos,Kokotos, Christoforos G.,Magrioti, Victoria,Dennis, Edward A.
experimental part, p. 3602 - 3610 (2010/08/06)
Group VIA calcium-independent phospholipase A2 (GVIA iPLA 2) has recently emerged as a novel pharmaceutical target. We have now explored the Structure-activity relationship between fluoroketones and GVIA iPLA2 inhibition. The presence of a naphthyl group proved to be of paramount importance. 1,1,1-Trifluoro-6-(naphthalen-2-yl)hexan-2-one (FKGK18) is the most potent inhibitor of GVIA iPLA2 (XI(50) = 0.0002) ever reported. Being 195 and >455 times more potent for GVIA iPLA 2 than for GIVA cPLA2 and GV sPLA2, respectively, makes it a valuable tool to explore the role of GVIA iPLA 2 in cells and in vivo models. 1,1,1,2,2,3,3-Heptafluoro-8- (naphthalene-2-yl)octan-4-one inhibited GVIA iPLA2 with a X I(50) value of 0.001 while inhibiting the other intracellular GIVA cPLA2 and GV sPLA2 at least 90 times less potently. Hexa- and octafluoro ketones were also found to be potent inhibitors of GVIA iPLA 2; however, they are not selective.
In situ alcohol oxidation - Wittig reactions using N-methoxy-N-methyl-2-(triphenylphosphoranylidine)acetamide: Application to the synthesis of a novel analogue of 5-oxo-eicosatetraenoic acid
Blackburn, Leonie,Kanno, Hisashi,Taylor, Richard J. K.
, p. 115 - 118 (2007/10/03)
Benzylic, allylic, propargylic and unactivated alcohols can be oxidised with activated manganese dioxide in the presence of N-methoxy-N-methyl-2-(triphenylphosphoranylidine)acetamide to generate directly the corresponding α,β-unsaturated Weinreb amides. Elaboration of the resulting Weinreb amides is also described, in particular as part of a new route to analogues of the arachidonic acid metabolite 5-oxo-6E,8Z,11Z,14Z-eicosatetraenoic acid.
