An in-depth study on ring-closing metathesis of carbohydrate-derived alpha-alkoxyacrylates: efficient syntheses of DAH, KDO, and 2-deoxy-beta-KDO.
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.
Hekking
Koen F W
KF
Institute for Molecules and Materials, Radboud University Nijmegen, Toernooiveld 1, NL-6525 ED Nijmegen, The Netherlands.
Moelands
Marcel A H
MA
van Delft
Floris L
FL
Rutjes
Floris P J T
FP
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
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