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

Author:
Vishwanatha, Thimmalapura M., Kurpiewska, Katarzyna, Kalinowska-Tłuścik, Justyna, Dömling, Alexander
Source:
Journal of organic chemistry 2017 v.82 no.18 pp. 9585-9594
ISSN:
1520-6904
Subject:
aldehydes, bioactive compounds, chemical reactions, cysteine, enantiomers, organic chemistry, thiazoles
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.
Agid:
5803016