Thallium(III)-Mediated Ring Contraction of cis-Octalins: An Approach for the Diastereoselective Construction of the nor-Bakkane Skeleton

ABSTRACT A new approach for the diastereoselective synthesis of CIS-hydrindanes bearing important structural features of the bakkane skeleton is described. The key step in such a sequence is a thallium trinitrate mediated oxidative rearrangement of CIS-octalins. The ring-contraction products thus obtained were elaborated in a diastereoselective fashion into hydrindanes bearing a quaternary center.