Catalytic synthesis of novel 4-C-glycosyl coumarins using a domino Heck reaction/lactonization process

A catalytic synthesis of novel 4-linked C-glycosyl coumarins was achieved using a domino Heck reaction/lactonization process. Methyl 3-glycosyl cinnamates were prepared from methyl 4-glycosyl-but-2-enoates using a panel of aryl iodides under Heck conditions. A direct application of this new methodology was made toward preliminary hemagglutination inhibition assays against galectins-1 and -3. C-Galactoside 30 had an IC50 of 313 mu M against galectin-1. (C) 2009 Elsevier Ltd. All rights reserved.