A literature review with 110 references is presented which examines the history of the chemistry of condensed tannins and the development of this chemistry in parallel with the development of modern analytical techniques. The role which these compounds play in the wine and brewing industries is discussed. An examination of the different synthetic routes applied to the isolation of condensed tannins, most notable procyanidin B3, is presented. Also investigations into the modes o f action for the format ion o f tannins in wine and beers is discussed with the implications behind their presence explained. An experimental section that examines two different synthetic routes for the formation of procyanidin B3 from the sta rting materia ls (+)-taxifolin and (+)- catechin is presented and the advantages and disadvantages outlined. New analytical methods for the monitoring of these reactions are presented along with the NMR spectra of recovered products which are explained and compared to data generated from literature sources. A method for the acetyla tion of the react ion products, thus stabilising them is presented along with the HPLC and NMR details explaining the results obtained. Finally two separate at tempts at synthesising procyanidin B3 via enzymatic oxidat ion are presented and discussed, and the two methods are evaluated.