Chemistry

When Your Sugar Needs a Ring

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Science  06 Jul 2001:
Vol. 293, Issue 5527, pp. 15
DOI: 10.1126/science.293.5527.15c

The C-aryl glycosides are an important class of naturally occurring antibiotics in which sugar groups are attached to a naphthol core of fused aromatic rings. Kaelin et al. have outlined two general strategies for synthesizing such molecules. The reaction of carbohydrate-derivatized furans with benzynes (deprotonated benzene derivatives generated with sec-butyl lithium under very cold conditions) via a Diels-Alder reaction creates a species in which one ring is bridged by an oxo group. Final products are formed by an acid-catalyzed rearrangement. Alternatively, the sugar group can be introduced by the palladium-catalyzed condensation of the oxo-bridged species with an iodoglycal. This latter reaction even works when the oxo-bridged species already contains one sugar substituent. — PDS

J. Am. Chem. Soc.,10.1021/ja0108640.

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