175212-45-0Relevant academic research and scientific papers
Anomeric oxygen to carbon rearrangements of alkynyl tributylstannane derivatives of furanyl (γ)- and pyranyl (δ)-lactols
Buffet, Marianne F.,Dixon, Darren J.,Ley, Steven V.,Reynolds, Dominic J.,Storer, R. Ian
, p. 1145 - 1154 (2007/10/03)
Tetrahydropyran and tetrahydrofuran containing natural products, drugs and agrochemicals often possess carbon-carbon bonds adjacent to the heteroatom. Consequently, new methods for the construction of anomeric carbon-carbon bonds are of considerable importance. We have devised a new strategy to access these systems that requires the treatment of O-glycoside alkynyl tributylstannane derivatives of furanyl and pyranyl lactols with Lewis acid to effect oxygen to carbon rearrangements. This leads to the formation of the corresponding carbon linked alkynol products that can be further manipulated to produce key structural motifs and building blocks for the assembly of complex molecules.
A novel and simple asymmetric synthesis of CMI-977 (LDP-977): A potent anti-asthmatic drug lead
Gurjar, Mukund K.,Murugaiah,Radhakrishna,Ramana,Chorghade, Mukund S.
, p. 1363 - 1370 (2007/10/03)
A practical gram scale asymmetric synthesis of CMI-977 is described. A tandem double elimination of an α-chlorooxirane and concomitant intramolecular nucleophilic substitution was used as the key step. Jacobsen hydrolytic kinetic resolution and Sharpless
A short and efficient stereoselective synthesis of the potent 5-lipoxygenase inhibitor, CMI-977
Dixon,Ley,Reynolds,Chorghade
, p. 1043 - 1053 (2007/10/03)
A short and efficient synthesis of the potent 5-lipoxygenase inhibitor CMI-977 has been accomplished, utilising an oxygen to carbon rearrangement of an anomerically linked alkynyl stannane tetrahydrofuranyl ether derivative as the key step.
A short and efficient stereoselective synthesis of the potent 5- lipoxygenase inhibitor CMI-977
Dixon, Darren J.,Ley, Steven V.,Reynolds, Dominic J.,Chorghade, Mukund S.
, p. 1955 - 1961 (2007/10/03)
A short and efficient synthesis of the potent 5-lipoxygenase inhibitor CMI-977 is described using as the key step a stereoselective anomeric oxygen to carbon rearrangement of an alkynyl stannane tetrahydrofuranyl ether derivative mediated by boron trifluoride etherate.
A versatile approach to anti-asthmatic compound CMI-977 and its six- membered analogue
Gurjar, Mukund K.,Krishna, L. Murali,Reddy, B. Sridhar,Chorghade, Mukund S.
, p. 557 - 560 (2007/10/03)
The synthesis of the anti-asthmatic compound CMI-977 is described. The tetrahydrofuran ring was effectively constructed by involving olefin metathesis while the stereoselective introduction of the 1-N- hydroxyureidylbut-3-yn-4-yl side-chain was achieved b
Synthesis of CMI-977, a potent 5-lipoxygenase inhibitor
Cai, Xiong,Chorghade, Mukund S.,Fura, Aberra,Grewal, Gurmit S.,Jauregui, Karen A.,Lounsbury, Heather A.,Scannell, Ralph T.,Yeh, C. Grace,Young, Michelle A.,Yu, Shaoxia,Guo, Liang,Moriarty, Robert M.,Penmasta, Raju,Rao, Munagala S.,Singhal, Rajesh K.,Song, Zhengzhe,Staszewski, James P.,Tuladhar, Sudersan M.,Yang, Sanmin
, p. 73 - 76 (2013/09/08)
CMI-977 is a potent 5-lipoxygenase inhibitor that intervenes in the production of leukotrienes and is presently being developed for the treatment of chronic asthma. It is a single enantiomer with an all-trans (2S,5S) configuration. Of the four isomers of CMI-977, the S,S isomer was found to have the best biological activity and was selected for further development. The enantiomerically pure product was synthesized on a 2-kg scale from (S)-(+)-hydroxymethyl-γ-butyrolactone.
