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Glycomimetic building blocks: a divergent synthesis of epimers of shikimic acid.

ABSTRACT: A divergent synthesis of (-)-4-epi-shikimic acid was developed. This route features a one-pot zinc-mediated reductive ring opening of an arabinofuranose followed by a Barbier reaction and culminates in a ring-closing metathesis. Functionalization of (-)-4-epi-shikimic acid via conjugate addition of a thiol occurs in high diastereoselectivity to afford a product with the features of fucosylated glycans.

SUBMITTER: Grim JC

PROVIDER: S-EPMC3166631 | biostudies-literature | 2011 Aug

REPOSITORIES: biostudies-literature

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Glycomimetic building blocks: a divergent synthesis of epimers of shikimic acid.

Grim Joseph C JC Garber Kathleen C A KC Kiessling Laura L LL

Organic letters 20110628 15

A divergent synthesis of (-)-4-epi-shikimic acid was developed. This route features a one-pot zinc-mediated reductive ring opening of an arabinofuranose followed by a Barbier reaction and culminates in a ring-closing metathesis. Functionalization of (-)-4-epi-shikimic acid via conjugate addition of a thiol occurs in high diastereoselectivity to afford a product with the features of fucosylated glycans. ...[more]

PMID: 21711006

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