Abstract
Samarium(II) iodide has been found to induce carbon-carbon bond cleavage in a number of bicyclo[2.2.1]heptane derivatives having 1,4-dicarbonyl moiety under conditions in which the 1,4-dicarbonyl moiety undergoes intramolecular pinacol coupling. This cleavage reaction offers routes to the synthesis of bridged eight membered rings and 1,3-disubstituted cyclopentanes, important building blocks for natural products synthesis.