title: 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.
authors.affiliation: Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, Wisconsin 53706, USA.
authors.forename: Joseph C
authors.initials: JC
authors.lastname: Grim
authors.forename: Kathleen C A
authors.initials: KC
authors.lastname: Garber
authors.forename: Laura L
authors.initials: LL
authors.lastname: Kiessling
mesh_terms: D040761:Biomimetic Materials / Q000737:chemistry*; D005643:Fucose / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D011134:Polysaccharides / Q000737:chemistry*; D012765:Shikimic Acid / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D011134:Polysaccharides; D005643:Fucose; D012765:Shikimic Acid