Synthesis of CMI-977, a Potent 5-Lipoxygenase Inhibitor^†

Xiong Cai,Mukund S. Chorghade,Aberra Fura,Gurmit S. Grewal,Karen A. Jauregui,Heather A. Lounsbury,Ralph T. Scannell,C. Grace Yeh,Michelle A. Young,Shaoxia Yu,Liang Guo,Robert M. Moriarty,Raju Penmasta,Munagala S. Rao, Rajesh K. Singhal,Zhengzhe Song,James P. Staszewski,Sudersan M. Tuladhar, Sanmin Yang

ORGANIC PROCESS RESEARCH & DEVELOPMENT（1999）

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摘要

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-gamma-butyrolactone.

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Synthesis of CMI-977, a Potent 5-Lipoxygenase Inhibitor†

Synthesis of CMI-977, a Potent 5-Lipoxygenase Inhibitor^†