Título Chemoenzymatic synthesis of carbasugars from iodobenzene
Autores Boyd, DR , Sharma, ND , MOREJÓN LLAMAS, NOEMÍ, Malone, JF , O'Dowd, CR , Allen, CCR
Publicación externa Si
Alcance Article
Naturaleza Científica
Cuartil JCR 2
Cuartil SJR 1
Impacto JCR 2.54700
Impacto SJR 1.29300
Fecha de publicacion 01/01/2005
ISI 229067300020
DOI 10.1039/b502009c
Abstract The versatile enantiopure cis-dihydrodiol metabolite 1, formed by bacterial metabolism of iodobenzene, has been used for the synthesis of the pyranose carbasugars (pseudosugars) carba-β-D-altropyranose 2, carba-α-L-galactopyranose 3, carba-β-D-idopyranose 4 and carba-β-L-glucopyranose 5. Substitution of the iodine atom by a carbomethoxy group, stereoselective catalytic hydrogenation of an α,β-unsaturated ester, and regioselective inversion of one or two allylic chiral centres are the key steps used in the synthesis of carbasugars 2-5. The relative and absolute configurations of compounds 2-5 were established by a combination of stereochemical correlation, X-ray crystallography and H-1-NMR spectroscopy.
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