Thallium(III)-mediated ring contraction of cis-octalins: An approach for the diastereoselective construction of the nor-bakkane skeleton

摘要

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.