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

✍ Scribed by 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

Book ID
121361703
Publisher
American Chemical Society
Year
1999
Tongue
English
Weight
103 KB
Volume
3
Category
Article
ISSN
1083-6160

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Synthesis of CMI-977, a Potent 5-Lipoxygenase Inhibitor. -A facile large-scale synthesis of the potent 5-lipoxygenase inhibitor CMI-977 (XI) in enantiomerically pure form starting from hydroxymethyl-γ-butyrolactone (I) derived from (S)-glutamic acid is described (yields given in g). -(CAI,

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-propoxy-S(N'-butyl-N'-hydroxyureidyl)phenyl]-S-(3,4.5-trimethoxyphenyl)tetrahydrofuran, was synthesized and was found to antagonize PAP receptor binding and inhibit S-lipoxygenase activity both in vitro and in vivo.

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A practical gram scale asymmetric synthesis of CMI-977 is described. A tandem double elimination of an a-chlorooxirane and concomitant intramolecular nucleophilic substitution was used as the key step. Jacobsen hydrolytic kinetic resolution and Sharpless asymmetric epoxidation protocols were applied