B. Branchaud, M. Meier
1988
Citations
0
Influential Citations
13
Citations
Journal
Tetrahedron Letters
Abstract
Abstract We report a synthesis of the ammonium salt of the 8-carbon monosaccharide 3-deoxy-(d)- manno -2-octulosonic acid (KDO) starting from (d)-mannose. The key C-C bond construction in our synthetic strategy is a novel alkyl cobaloxime mediated radical alkyl-alkenyl cross coupling of α-ethoxyacrylonitrile with an alkyl cobaloxime derivative of D-mannose. KMnO 4 unmasking of the latent functionality in the α-ethoxyacrylonitrile moiety provides the α-hydroxyester moiety necessary for completion of the KDO synthesis.