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Concise Synthesis of Macrocycles by Multicomponent Reactions.

ABSTRACT: A short reaction pathway was devised to synthesize a library of artificial 18-27-membered macrocycles. The five-step reaction sequence involves ring opening of a cyclic anhydride with a diamine, esterification, coupling with an amino acid isocyanide, saponification, and, finally, macro-ring closure using an Ugi or, alternatively, a Passerini multicomponent reaction. Three out of the five steps allow for the versatile introduction of linker elements, side chains, and substituents with aromatic, heteroaromatic, and aliphatic character. The versatile pathway is described for 15 different target macrocycles on a mmol scale. Artificial macrocycles have recently become of great interest due to their potential to bind to difficult post-genomic targets.

SUBMITTER: Abdelraheem EMM

PROVIDER: S-EPMC6706064 | biostudies-literature | 2018 Mar

REPOSITORIES: biostudies-literature

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Concise Synthesis of Macrocycles by Multicomponent Reactions.

Abdelraheem Eman M M EMM Khaksar Samad S Dömling Alexander A

Synthesis 20180110 5

A short reaction pathway was devised to synthesize a library of artificial 18-27-membered macrocycles. The five-step reaction sequence involves ring opening of a cyclic anhydride with a diamine, esterification, coupling with an amino acid isocyanide, saponification, and, finally, macro-ring closure using an Ugi or, alternatively, a Passerini multicomponent reaction. Three out of the five steps allow for the versatile introduction of linker elements, side chains, and substituents with aromatic, h ...[more]

PMID: 31439965

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