Cyclization/alkoxy radical fragmentation tandem: An efficient approach to the synthesis of bridged cyclooctane derivatives

In this paper an efficient synthetic approach to bridged cyclooctanone framework is described, which is based on cyclization/alkoxy radical fragmentation as a tactical combination of reactions. While the hypoiodite reaction of alcohol 11 proceeds in a normal fashion, the hypobromite reaction of the same precursor unexpectedly affords dibromo derivative 14, which, in turn, shows unusual reactivity in the presence of cesium acetate