Synthesis of diphenyl ether models of thyroid hormones. Diphenyl ethers linked to the 3-oxo-2-azabicyclo [2.2. 1] heptane ring system as substrates for conformational …

…, HL Ammon, L Liu, E Colicelli, P Ravi…

Index: Mazzocchi, Paul H.; Ammon, Herman L.; Liu, Leslie; Colicelli, Elena; Ravi, Prasad; Burrows, Elizabeth Journal of Organic Chemistry, 1981 , vol. 46, # 22 p. 4530 - 4536

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Citation Number: 5

Abstract

A series of diphenyl ethers linked to 2-azabicyclo [2.2. 2] octan-3-ones and 2-azabicyclo [2.2. l] 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 ero-6-tosyloxy bicyclic lactam with the corresponding phenoxide which results in formation of the phenyl ether with retention of stereochemistry. This double-inversion ...