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Artificial Macrocycles by Ugi Reaction and Passerini Ring Closure.

ABSTRACT: Artificial macrocycles can be convergently synthesized by a sequence of an Ugi multicomponent reaction (MCR) followed by an intramolecular Passerini MCR used to close the macrocycle. Significantly, in this work, the first intramolecular macrocyclization through a Passerini reaction is described. We describe 21 macrocycles of a size of 15-20. The resulting macrocyclic depsipeptides are model compounds for natural products and could find applications in drug discovery.

SUBMITTER: Abdelraheem EM

PROVIDER: S-EPMC6280654 | biostudies-other | 2016 Oct

REPOSITORIES: biostudies-other

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Artificial Macrocycles by Ugi Reaction and Passerini Ring Closure.

Abdelraheem Eman M M EM Kurpiewska Katarzyna K Kalinowska-Tłuścik Justyna J Dömling Alexander A

The Journal of organic chemistry 20160915 19

Artificial macrocycles can be convergently synthesized by a sequence of an Ugi multicomponent reaction (MCR) followed by an intramolecular Passerini MCR used to close the macrocycle. Significantly, in this work, the first intramolecular macrocyclization through a Passerini reaction is described. We describe 21 macrocycles of a size of 15-20. The resulting macrocyclic depsipeptides are model compounds for natural products and could find applications in drug discovery. ...[more]

PMID: 27598302

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