Canadian journal of chemistry

Preparation of exo-6-benzyl-exo-2-(m-hydroxyphenyl)-1-dimethylaminomethylbicyclo [2.2. 2.] octane. A non-peptide mimic of enkephalins

PC Bélanger, C Dufresne

Index: Belanger, Patrice C.; Dufresne, Claude Canadian Journal of Chemistry, 1986 ,  vol. 64, p. 1514 - 1520

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Citation Number: 49

Abstract

A model for the active conformation of methionine enkephalin was derived from computer modeling. From this model, a target was designed and synthesized using bicyclo [2.2. 2] octane as a structural template. Thus, a key intermediate, exo-6-benzoyl-1- carboethoxybicyclo [2.2. 2]-2-octene was prepared via a Diels-Alder reaction using ethyl dihydrobenzoate and phenylvinylketone. It was subsequently modified to exo-6-benzyl-1- ...