Synthesis of Diphenyl Ether Models of Thyroid Hormones. Diphenyl Ethers Linked to the 3-Oxo-2-azabicycloheptane Ring System as Substrates for Conformational Analysis

Article abstract of DOI:10.1021/jo00335a042

A series of diphenyl ethers linked to 2-azabicyclo<2.2.2>octan-3-ones and 2-azabicyclo<2.2.1>heptan-3-ones were synthesized as substrates for conformational analysis using the lanthanide shift reagent NMR technique.The materials were prepared by displacement of the exo-6-tosyloxy bicyclic lactam with the corresponding phenoxide which results in formation of the phenyl ether with retention of stereochemistry.This double-inversion process presumably involves anchimeric assistance by the lactam nitrogen.The synthesis and properties of a number of these systems are described.Complete 13C assignments for the series are presented.