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Total synthesis of 3-deoxy-D-manno-2-octulosonic acid (KDO) and 2-deoxy-beta-KDO
1Department of Chemistry, University of Wisconsin-Madison 53706-1396, USA. burke@chem.wisc.edu
Organic Letters
|May 24, 2000
Abstract:
[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.