Solid-Phase Synthesis of Diverse Macrocycles by Regiospecific 2-Pyridone Formation: Scope and Applications

This study introduces a novel solid-phase macrocyclization method generating 2-pyridone rings. This method relies on the intramolecular condensation between secondary and tertiary dimethoxy-propionic amide units. This selective reaction leads to the formation of a single well-defined regioisomer. The method demonstrates remarkable efficiency in producing diverse peptidic and nonpeptidic bioactive targets, paving the way for the development of innovative macrocycle libraries featuring the 2-pyridone unit.

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Publication Details

Journal
JACS Au
Published
2024-08-12
DOI
https://doi.org/10.1021/jacsau.4c00352
Citations
3
Primary Topic
Chemical Synthesis and Analysis
Type
article
Field-Weighted Citation Impact
0.70

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article

Solid-Phase Synthesis of Diverse Macrocycles by Regiospecific 2-Pyridone Formation: Scope and Applications

Thomas Kodadek, Skander Abboud
3 citations
JACS Au
Chemical Synthesis and Analysis
0.70
article

Solid-Phase Synthesis of Diverse Macrocycles by Regiospecific 2-Pyridone Formation: Scope and Applications

Thomas Kodadek, Skander Abboud
article en
3 citations

Abstract

This study introduces a novel solid-phase macrocyclization method generating 2-pyridone rings. This method relies on the intramolecular condensation between secondary and tertiary dimethoxy-propionic amide units. This selective reaction leads to the formation of a single well-defined regioisomer. The method demonstrates remarkable efficiency in producing diverse peptidic and nonpeptidic bioactive targets, paving the way for the development of innovative macrocycle libraries featuring the 2-pyridone unit.

JACS AuVol. 4(8)
Scripps (United States) (US)
National Cancer Institute
Openalex Percentile: Top 30%
Chemical Synthesis and Analysis
0.70
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