title: An in-depth study on ring-closing metathesis of carbohydrate-derived alpha-alkoxyacrylates: efficient syntheses of DAH, KDO, and 2-deoxy-beta-KDO.
abstract: Novel, efficient synthetic pathways to DAH, KDO, and 2-deoxy-beta-KDO are described. Ring-closing metathesis (RCM) of highly functionalized alpha-alkoxyacrylate fragments resulted in a series of synthetically versatile oxygen heterocyclic intermediates. Further functionalization of the resulting enol ether double bond and subsequent deprotection provided the natural products in high overall yields, starting from commercially available protected sugars.
authors.affiliation: Institute for Molecules and Materials, Radboud University Nijmegen, Toernooiveld 1, NL-6525 ED Nijmegen, The Netherlands.
authors.forename: Koen F W
authors.initials: KF
authors.lastname: Hekking
authors.forename: Marcel A H
authors.initials: MA
authors.lastname: Moelands
authors.forename: Floris L
authors.initials: FL
authors.lastname: van Delft
authors.forename: Floris P J T
authors.initials: FP
authors.lastname: Rutjes
mesh_terms: D000179:Acrylates / Q000737:chemistry*; D000478:Alkylation; D002241:Carbohydrates / Q000737:chemistry*; D002384:Catalysis; D007536:Isomerism; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry*; D013400:Sugar Acids / Q000138:chemical synthesis* / Q000737:chemistry; D013403:Sugar Phosphates / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000179:Acrylates; D002241:Carbohydrates; D013400:Sugar Acids; D013403:Sugar Phosphates; C002532:2-keto-3-deoxyoctonate; C013469:3-deoxy-D-arabino-heptulosonate-7-phosphate; C036658:acrylic acid; D010100:Oxygen