Small ring constrained peptidomimetics. Synthesis of epoxy peptidomimetics, inhibitors of cysteine proteases

…, A Porcheddu, L Quaranta, G Reginato…

Index: Demarcus; Ganadu; Mura; Porcheddu; Quaranta; Reginato; Taddei Journal of Organic Chemistry, 2001 , vol. 66, # 3 p. 697 - 706

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Citation Number: 29

Abstract

Different dipeptide analogues containing an oxirane ring in the place of the peptidic bond were prepared starting from naturally occurring amino acids. N-Fmoc-amino aldehydes were transformed into the corresponding methoxyvinyl derivatives through a Wittig reaction, and the addition of PhSeCl gave a series of different α-phenylselenyl aldehydes. Mukajiama reaction with silylketene acetals gave an intermediate product that was finally transformed ...