Synthesis of Epibatidine Analogues Having a 2??Substituted 2??Azabicyclo [2.2. 2] octane Skeleton

I Wauters, A De Blieck, K Muylaert…

Index: Wauters, Iris; De Blieck, Ann; Muylaert, Koen; Heugebaert, Thomas S. A.; Stevens, Christian V. European Journal of Organic Chemistry, 2014 , vol. 2014, # 6 p. 1296 - 1304

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Abstract

Abstract The synthesis of 1-cyano-2-aza-[2.2. 2] bicyclooctanes has been studied using the dynamic cyanide addition to cyclohexanone derivatives. These compounds were further elaborated into a new class of epibatidine derivatives from which a number of examples were fully deprotected to give the potentially active compounds. The highly hydrophilic character of the compounds resulted in a difficult isolation and purification of the ...