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Synthesis of a Conformationally Rigid Analogue of 2-Aminoadipic Acid Containing an 8-Azabicyclo[3.2.1]octane Skeleton

  作者 KUBYSHKIN VLADIMIR S; MYKHAILIUK PAVEL K; ULRICH ANNE S; KOMAROV IGOR  
  选自 期刊  Synthesis;  卷期  2009年-19;  页码  3327-3331  
  关联知识点  
 

[摘要]A new, conformationally rigid analogue of 2-aminoadipic acid, 8-[(benzyloxy)carbonyl]-3-methylene-8-azabicyclo[3.2.1]octane-1,5-dicar boxylic acid, is synthesized from dimethyl rac-2,5-dibromohexanedioate. The key steps involve alkylation-cyclization of 1-benzyl 2,5-dimethyl pyrrolidine-1,2,5-tricarboxylate with 3-chloro-2-(chloromethyl)prop-1-ene to yield the 8-azabicyclo[3.2.1]octane skeleton.

 
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