Remote Electronic Control in the Regioselective Reduction of Succinimides: A Practical, Scalable Synthesis of EP4 Antagonist MF-310
The Journal of Organic Chemistry2009Vol. 74(17), pp. 6863–6866
Citations Over Time
Carmela Molinaro, Danny Gauvreau, Gregory Hughes, Stephen Y. W. Lau, Sophie Lauzon, Rémy Angelaud, Paul O’Shea, Jacob M. Janey, Michael Palucki, Scott Hoerrner, Conrad E. Raab, Rick R. Sidler, Michel Belley, Yongxin Han
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, preparation of cyclopropane carboxylic acid 3 via a Corey-Chaykovsky cyclopropanation, and a short synthesis of sulfonamide 5.
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