Synthesis of Caryose, the Carbocyclic Monosaccharide Component of the Lipopolysaccharide from Pseudomonas caryophylli.

Abstract 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 SmI 2 -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.