Anodic oxidations of electron-rich olefins: radical cation based approaches to the synthesis of bridged bicyclic ring skeletons

The use of intramolecular anodic olefin coupling reactions for building bic yclo[3.2.1]octane ring skeletons has been examined. While simple model syst ems using bis enol ether substrates readily led to the formation of bicycli c products, application of the reactions to total synthesis efforts were hi ndered by reactions forming dimethoxy acetal groups at both the terminating and initiating ends of the cyclization reactions. In an effort to solve th is problem, ketene acetal based initiating groups have been studied. The us e of a ketene dithioacetal group proved especially useful for this purpose. (C) 2001 Elsevier Science Ltd. All rights reserved.