Issue 10, 2005

Chemoenzymatic synthesis of carbasugars from iodobenzene

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 25. The relative and absolute configurations of compounds 25 were established by a combination of stereochemical correlation, X-ray crystallography and 1H-NMR spectroscopy.

Graphical abstract: Chemoenzymatic synthesis of carbasugars from iodobenzene

Supplementary files

Article information

Article type
Paper
Submitted
08 Feb 2005
Accepted
15 Mar 2005
First published
18 Apr 2005

Org. Biomol. Chem., 2005,3, 1953-1963

Chemoenzymatic synthesis of carbasugars from iodobenzene

D. R. Boyd, N. D. Sharma, N. M. Llamas, J. F. Malone, C. R. O'Dowd and Christopher. C. R. Allen, Org. Biomol. Chem., 2005, 3, 1953 DOI: 10.1039/B502009C

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