Strategies and Methods for the Syntheses of Natural Oligomeric Stilbenoids and Analogues

This review covers synthetic work carried out in the field of stilbene and oligostilbene chemistry. It includes a brief overview of the methods used for the synthesis of monomeric stilbenoids. The production of oligomeric species by means of enzymatic or microbial conversion is examined in detail. Biomimetic syntheses of stilbene oligomers are then scrutinised. Most of the work is based on the dimerisation of stilbenoid monomers with help of one-electron oxidants or through acid catalysis. Mechanistic interpretations of the oxidative couplings observed by the various groups are proposed and suggest that the outcome of these reaction be guided by the hard and soft acid and base (HSAB) principle together with supramolecular interactions between the reacting stilbenoid monomers. Eventually, the few non-biomimetic full syntheses are presented and their strategies analysed.