Cysteine Isocyanide in Multicomponent Reaction: Synthesis of Peptido-Mimetic 1,3-Azoles

Thimmalapura M Vishwanatha, Katarzyna Kurpiewska, Justyna Kalinowska-Tłuścik, Alexander Dömling

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Abstract

An alternative approach toward the simple and robust synthesis of highly substituted peptidic thiazole derivatives using Ugi-multicomponent reaction (U-MCR) is described. Thus, we introduced the enantiopure (R)-2-methyl-2-isocyano-3-(tritylthio)propanoate as a novel class of isocyanide in MCR. This bifunctional isocyanide was found to undergo mild cyclodehydration to afford thiazole containing peptidomimetics in a short synthetic sequence. Several examples of bis-heterocyclic rings were also synthesized through the proper choice of the aldehyde component in the U-4CR. The method opens a wide range of applications toward the synthesis of nonribosomal natural products and other bioactive compounds.

Original languageEnglish
Pages (from-to)9585-9594
Number of pages10
JournalThe Journal of Organic Chemistry
Volume82
Issue number18
DOIs
Publication statusPublished - 15-Sep-2017

Keywords

  • Journal Article

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