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First stereoselective synthesis of potassium aeschynomate and its no-natural stereomers |
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| Authors: | Stéphanie Claudel Pierre Mutzenardt Philippe Coutrot |
| Institution: | a Laboratoire de Chimie Organique Biomoléculaire, UMR 7565, Université Henri Poincaré, Nancy 1, BP 239, 54506 Vandoeuvre-lès-Nancy cédex, France b Laboratoire de Chimie Biomoléculaire, UMR 5032, ERT 5, 8 rue de l'Ecole Normale, 34296 Montpellier, France c Laboratoire de Méthodologie RMN, UMR 7565, Université Henri Poincaré, Nancy 1, BP 239, 54506 Vandoeuvre-lès-Nancy cédex, France |
| Abstract: | The synthesis of potassium aeshynomate and its non-natural stereomers was achieved using the Sharpless catalytic asymmetric dihydroxylation of (Z) or (E) vinylogous glycine as the key step. The resulting γ-amino α,β-dihydroxyester stereomer was deprotected and coupled with the caffeic acid to afford stereoselectively potassium aeshynomate or its stereomers. A detailed study of the NMR data of the different stereomers is reported that corrects the literature data. |
| Keywords: | Potassium aeshynomate Vinylogous peptides Aminoaldehydes Horner reaction Asymmetric dihydroxylation Natural product |
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