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Formal Synthesis of (+)-3-Deoxy- d - g lycero - d - g alacto -2-nonulosonic Acid (KDN) via Desymmetrization by Ring-Closing Metathesis

โœ Scribed by Burke, Steven D.; Voight, Eric A.

Book ID
126876366
Publisher
American Chemical Society
Year
2001
Tongue
English
Weight
69 KB
Volume
3
Category
Article
ISSN
1523-7060

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Formal synthesis of (โˆ’)-N-acetylneuramin
Formal synthesis of (โˆ’)-N-acetylneuraminic acid (Neu5Ac) via desymmetrization by ring-closing metathesis
โœ Eric A Voight; Christian Rein; Steven D Burke ๐Ÿ“‚ Article ๐Ÿ“… 2001 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 83 KB

A formal total synthesis of (-)-N-acetylneuraminic acid (Neu5Ac), the most naturally abundant sialic acid, has been accomplished using a rigid 6,8-dioxabicyclo[3.2.1]octane template for stereoselective introduction of all oxygen and nitrogen functionality. The template was obtained via a novel ketal