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

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

Source and publish data:

Tetrahedron p. 11767 - 11780 (1997)

Update date:2022-08-03

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Authors:

Adinolfi, Matteo

Barone, Gaspare

Iadonisi, Alfonso

Mangoni, Lorenzo

Manna, Rosario

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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.

Full text of DOI:10.1016/S0040-4020(97)00743-6

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