Asymmetric syntheses of a GPR40 receptor agonist via diastereoselective and enantioselective conjugate alkynylation |
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Authors: | Jacqueline CS Woo Shawn D Walker Margaret M Faul |
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Institution: | Department of Chemical Process Research and Development, Amgen Inc., One Amgen Center Drive, Thousand Oaks, CA 91320, USA |
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Abstract: | Two asymmetric methods to synthesize a potent GPR40 receptor agonist are reported. Both synthetic routes utilize readily available, inexpensive starting materials and reagents. The first route relies on a highly diastereoselective conjugate alkynylation of an ephedrine-derived oxazepanedione acceptor. The second route features the enantioselective alkynylation of a Meldrum’s acid-derived acceptor mediated by a chiral zinc cinchonidine reagent. |
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Keywords: | GPR40 Conjugate addition Diastereoselective Enantioselective Oxazepanedione Cinchonidine β-Alkynyl acid Zincate |
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