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- W2024274612 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 involved application of a catalytic Meerwein arylation reaction between 2-nitro-4-trifluoromethoxyaniline and isopropenyl acetate and subsequent reductive cyclization. The α-aryloxybutanoic acid was prepared via an asymmetric hydrogenation of the corresponding α-aryloxy-α,β-unsaturated acid. Tetrabutylammonium iodide-catalyzed coupling of the two fragments and ester hydrolysis completed the convergent synthesis. The described convergent synthesis was used to prepare >3 kg of drug substance 1 in 50% overall yield and with >99.5% ee." @default.
- W2024274612 created "2016-06-24" @default.
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- W2024274612 date "2009-03-09" @default.
- W2024274612 modified "2023-10-17" @default.
- W2024274612 title "Practical, Highly Convergent, Asymmetric Synthesis of a Selective PPARγ Modulator" @default.
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- W2024274612 doi "https://doi.org/10.1021/op8002882" @default.
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