Glucosinolates: The synthetic approach

Acting generally as bio-precursors of isothiocyanates, glucosinolates (GLs) are important thiosaccharidic metabolites which occur in all plant families of the order Brassicales namely in our daily vegetables. All known GLs (ca 120 characterized molecules) display a remarkable structural homogeneity invariably based on a p-D-glucopyrano unit and an O-sulfated anomeric (Z)-thiohydroximate function connected to a side chain which constitution, depending on plant species, is the sole structural variant. Dedicated extractive methods allow one to isolate a number of GLs from adequate plant material, but in many cases, organic synthesis brings crucial help for the production of natural GLs. In other respects, synthesis is the only way to elaborate a diversified range of artificial GL analogues. This account summarizes the varied synthetic approaches developed by us and by others since the early 1960s. (C) 2010 Academie des sciences. Published by Elsevier Masson SAS. All rights reserved.