Total synthesis of 3-deoxy-D-manno-2-octulosonic acid (KDO) and 2-deoxy-beta-KDO.
[formula: see text] Total syntheses of KDO and 2-deoxy-beta-KDO are reported. The C2-symmetric dienediol 4 was desymmetrized by conversion to its corresponding 1,4-dioxanone 5. Ireland-Claisen rearrangement of 5 provided the 6-vinyldihydropyran-2-carboxylate template 6. Double-Sharpless asymmetric dihydroxylation gave the tetraol 7a, which was converted to KDO and 2-deoxy-beta-KDO using methods similar to those previously reported. This synthetic scheme provides a flexible route to KDO and KDO analogues.
Burke
S D
SD
Department of Chemistry, University of Wisconsin-Madison 53706-1396, USA. burke@chem.wisc.edu
Sametz
G M
GM
D006090:Gram-Negative Bacteria / Q000737:chemistry; D008070:Lipopolysaccharides / Q000737:chemistry; D013400:Sugar Acids / Q000138:chemical synthesis*
D008070:Lipopolysaccharides; D013400:Sugar Acids; C002532:2-keto-3-deoxyoctonate; C052138:2,6-anhydro-3-deoxyoctonate