Skeletal rearrangements of camphor are well-known, however, those involving camphorquinone, its sibling, are rare. We have found that the diol derived from allylated camphorquinone undergoes iodine or bromine mediated deep-seated skeletal rearrangement to provide an interesting tricyclic ring system. The iodo group in the rearranged product provided convenient leverage for further functionalization. For example, it was converted into an azide and the azide was subjected to copper(i) mediated Huisgen 1,3-dipolar cycloaddition with acetylenes to obtain a terpene-triazole conjugate.
This journal is © The Royal Society of Chemistry.