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Formal synthesis of (−)-N-acetylneuraminic acid (Neu5Ac) via desymmetrization by ring-closing metathesis

✍ Scribed by Eric A Voight; Christian Rein; Steven D Burke

Book ID: 104231957
Publisher: Elsevier Science
Year: 2001
Tongue: French
Weight: 83 KB
Volume: 42
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)01912-8

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✦ Synopsis

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 ketalization/ring-closing metathesis bond construction strategy, taking advantage of an advanced intermediate in our KDN synthesis to complete the efficient assembly of Neu5Ac.

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