226226-37-5Relevant articles and documents
Total synthesis of 3-deoxy-D-manno-2-octulosonic acid (KDO) and 2-deoxy-β-KDO
Burke, Steven D.,Sametz, Geoffrey M.
, p. 71 - 74 (1999)
(equation presented) Total syntheses of KDO and 2-deoxy-β-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-β-KDO using methods similar to those previously reported. This synthetic scheme provides a flexible route to KDO and KDO analogues.
