Synthesis of conformationally constrained amino acid and peptide derivatives

…, N Bannister, M Bernad, S Blanchard…

Index: Bailey; Bannister; Bernad; Blanchard; Boa Journal of the Chemical Society. Perkin Transactions 1, 2001 , # 24 p. 3245 - 3251

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Abstract

6-Benzylpiperazine-2, 3, 5-trione 5, a cyclic phenylalanine derivative, can be selectively and sequentially alkylated at N4, C6 and N1 to provide a range of conformationally constrained phenylalanine mimetics. Alkylation at C6, the α-carbon of the phenylalanine moiety is achieved under mild conditions and gives rise to Phe derivatives posessing a dialkylated α- carbon. Alkylation of piperazine 5 using methyl bromoacetate and ethyl bromopropionate ...