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Modular Synthesis of Triazole‐Containing Triaryl α‐Helix Mimetics
Author(s) -
Ehlers Ina,
Maity Prantik,
Aubé Jeffrey,
König Burkhard
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201001531
Subject(s) - chemistry , alkyne , combinatorial chemistry , azide , triazole , modular design , scaffold , click chemistry , side chain , stereochemistry , organic chemistry , catalysis , computer science , programming language , polymer
We describe novel scaffold designs for nonpeptidic α‐helix mimetics. The tricyclic scaffolds contain triazoles and reproduce amino acid side chains i , i +3, and i +7. The three different scaffolds are synthetically readily accessible, allow the introduction of further substituents to increase the versatility, and are suitable for library design. A modular synthesis route using Cu I ‐ and Ru II ‐catalyzed azide–alkyne [3+2] cycloadditions as central steps was developed. To demonstrate the methodology, we have prepared a library of compounds containing all three scaffolds.