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.

Keywords

bakkanes - ring contraction - thallium(III) - hydrindanes - oxidative rearrangement

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The X-ray data have been deposited at the Cambridge Crystallographic Data Centre and allocated the deposition number CCDC 605577.