Synthesis of caryose, the carbocyclic monosaccharide component of the lipopolysaccharide from pseudomonas caryophylli

Article abstract of DOI:10.1016/S0040-4020(97)00743-6

The structure of the novel natural carbocylic monosaccharide caryose (4,8-cyclo-3,9-dideoxy-L- erythro-D-ido-nonose) has been confirmed through a synthesis whose key steps are the SmI₂-mediated cyclization of a ketoaldehyde derived from 3,4,5-tri-O-benzyl-1-deoxy-D-iditol, the mild oxidation of the obtained cis-1,2-diol and the diasteroselective allylation of the resulting ketol.