Abstract
A combination of the Passerini reaction and copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC, click reaction) was used to synthesize triazole-containing macrocyclic depsipeptides. The key factors determining the direction of macrocyclization are the chain length of the initial depsipeptide and the presence of rigid fragments therein. The proposed strategy makes it possible to obtain monomeric (12–13-membered) and dimeric (24–28-membered) triazole-containing cyclic depsipeptides in up to 97% yield.
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24 November 2020
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V.G. Nenajdenko thanks the Russian Foundation for Basic Research (project no. 18-53-34002) for financial support.
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Kutovaya, I.V., Nenajdenko, V.G. Synthesis of Macrocyclic Depsipeptides via the Passerini–Click Reaction Strategy. Russ J Org Chem 56, 559–568 (2020). https://doi.org/10.1134/S1070428020040016
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DOI: https://doi.org/10.1134/S1070428020040016