Three-Step Synthesis of Sialic Acids and Derivatives

Authors

  • Zhangyong Hong Dr.,

    1. Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-2409
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  • Lei Liu Dr.,

    1. Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-2409
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  • Che-Chang Hsu Dr.,

    1. Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-2409
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  • Chi-Huey Wong Prof.

    1. Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA, Fax: (+1) 858-784-2409
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  • This work was supported by the National Institutes of Health. We thank Dr. Lisa Whalen for proofreading the manuscript.

Abstract

original image

Flexibel und effizient werden Sialinsäuren wie L-N-Acetylneuraminsäure (siehe Bild) in nur drei Stufen synthetisiert: 1) Vinylierung einer Aldose durch eine modifizierte Petasis-Kupplung, 2) 1,3-dipolare Cycloaddition mit einem Nitron zum Aufbau eines Isoxazolidinrings und 3) basenkatalysierte β-Eliminierung und Öffnung des Isoxazolidinrings zur γ-Hydroxy-α-ketosäure.

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