First stereoselective synthesis of potassium aeschynomate and its no-natural stereomers

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 affo...

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Bibliographic Details
Published in:Tetrahedron 2006-02, Vol.62 (8), p.1787-1798
Main Authors: Claudel, Stéphanie, Olszewski, Tomasz Krzysztof, Mutzenardt, Pierre, Aroulanda, Christie, Coutrot, Philippe, Grison, Claude
Format: Article
Language:English
Subjects:
Aminoaldehydes
Asymmetric dihydroxylation
Chemical Sciences
Horner reaction
Natural product
or physical chemistry
Organic chemistry
Potassium aeshynomate
Theoretical and
Vinylogous peptides
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Summary: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. Graphical Abstract
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2005.11.051