Remote Electronic Control in the Regioselective Reduction of Succinimides: A Practical, Scalable Synthesis of EP4 Antagonist MF-310

…, S Lauzon, R Angelaud, PD O'Shea…

Index: Molinaro, Carmela; Gauvreau, Danny; Hughes, Gregory; Lau, Stephen; Lauzon, Sophie; Angelaud, Remy; O'Shea, Paul D.; Janey, Jacob; Palucki, Michael; Hoerrner, Scott R.; Raab, Conrad E.; Sidler, Rick R.; Belley, Michel; Han, Yongxin Journal of Organic Chemistry, 2009 , vol. 74, # 17 p. 6863 - 6866

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Citation Number: 8

Abstract

A practical large-scale chromatography-free synthesis of EP4 antagonist MF-310, a potential new treatment for chronic inflammation, is presented. The synthetic route provided MF-310 as its sodium salt in 10 steps and 17% overall yield from commercially available pyridine dicarboxylate 7. The key features of this sequence include a unique regioselective reduction of succinimide 2 controlled by the electronic properties of a remote pyridine ring, ...