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

✍ Scribed by Matteo Adinolfi; Gaspare Barone; Alfonso Iadonisi; Lorenzo Mangoni; Rosario Manna

Book ID
104207992
Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
610 KB
Volume
53
Category
Article
ISSN
0040-4020

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✦ Synopsis

The structure of the novel natural carbocylic monosa~zclmride ca~'ose (4,8-cyclo-3.9-dideox3'-Lerythro-D-ido-nonose) has been confirmed through a synthesis whose key steps are the SmI2-mediated cyclization ofa ketoaldehyde derived from 3,4,5-tri-O-benzyl-l-deoxy-D-iditol, the mild oxidation of the obtained cis-l,2-dioi and the diasteroselective allylation of the resulting ketol.

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