Practical, highly convergent, asymmetric synthesis of a selective PPARγ modulator

PE Maligres, GR Humphrey, JF Marcoux…

Index: Maligres, Peter E.; Humphrey, Guy R.; Marcoux, Jean-Francois; Hillier, Michael C.; Zhao, Dalian; Krska, Shane; Grabowski, Edward J.J. Organic Process Research and Development, 2009 , vol. 13, # 3 p. 525 - 534

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Citation Number: 19

Abstract

A practical, highly convergent, asymmetric synthesis of a selective PPARγ modulator 1 is described. The inhibitor contains two key components, a 6-trifluoromethoxy-3-acylindole (6) and (R)-α-aryloxybutanoic acid derivative (10). Two methods were developed to overcome the regioselectivity issues encountered in the preparation of the 6-substituted indole. The first involved an intramolecular Heck reaction of an iodoaryl enamine. The second ...