Issue 24, 2021

Facile construction of peptidomimetics by sequential C–S/C–N bond activation of Ugi-adducts

Abstract

A novel selectively sequential C–S/C–N bond activation is presented. Through the combination of an Ugi-4CR and sequential C–S/C–N bond cleavage, diverse peptidomimetics containing a primary amide are prepared in a rapid, highly efficient and step-economical manner. This approach exhibits high yield, excellent chemoselectivity and functional group tolerance. Compounds derived from the pharmaceuticals febuxostat, probenecid and memantine as well as β-amino acid are prepared. This method provides a new direction for the synthesis of peptidomimetics.

Graphical abstract: Facile construction of peptidomimetics by sequential C–S/C–N bond activation of Ugi-adducts

Supplementary files

Article information

Article type
Research Article
Submitted
23 Sep 2021
Accepted
29 Oct 2021
First published
30 Oct 2021

Org. Chem. Front., 2021,8, 6968-6973

Facile construction of peptidomimetics by sequential C–S/C–N bond activation of Ugi-adducts

C. Liu, L. Song, V. A. Peshkov and E. V. Van der Eycken, Org. Chem. Front., 2021, 8, 6968 DOI: 10.1039/D1QO01438B

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