'Aromatic ring umpolung', a rapid access to the main core of several natural products

Treatment of various substituted phenols in the presence of (diacetoxyiodo)benzene promotes the formation of a phenoxenium ion, a very electrophilic species able to react with various nucleophiles leading rapidly to a plethora of different cores present in natural products via several novel oxidative processes. This strategy fits within the concept of 'aromatic ring umpolung': in this paper a personal account by our laboratory on this thematic is described. (C) 2010 Elsevier Ltd. All rights reserved.