Concise Synthesis of Azaphenanthrene Alkaloid Eupolauramine Via Au(I)‐Catalyzed Cycloisomerization and Intramolecular Ullmann‐Type Coupling Reaction

ABSTRACT A concise and efficient synthesis of the γ‐lactam‐fused azaphenanthrene alkaloid eupolauramine has been achieved. The key feature of the synthesis involves Au(I)‐catalyzed cycloisomerization of N ‐naphthyl aminobutynamide intermediate and subsequent intramolecular Ullmann‐type coupling reaction. This study clearly demonstrated the usefulness of coinage metal‐catalyzed cycloisomerization strategy in the construction of architecturally sophisticated pyridine‐fused heterocyclic scaffolds.

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Journal
Journal of Heterocyclic Chemistry
Published
2024-09-02
DOI
https://doi.org/10.1002/jhet.4889
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
0.00

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article

Concise Synthesis of Azaphenanthrene Alkaloid Eupolauramine Via Au(I)‐Catalyzed Cycloisomerization and Intramolecular Ullmann‐Type Coupling Reaction

Eunyeong Kim, Young Taek Han
Journal of Heterocyclic Chemistry
Catalytic C–H Functionalization Methods
article

Concise Synthesis of Azaphenanthrene Alkaloid Eupolauramine Via Au(I)‐Catalyzed Cycloisomerization and Intramolecular Ullmann‐Type Coupling Reaction

Eunyeong Kim, Young Taek Han
article en

Abstract

ABSTRACT A concise and efficient synthesis of the γ‐lactam‐fused azaphenanthrene alkaloid eupolauramine has been achieved. The key feature of the synthesis involves Au(I)‐catalyzed cycloisomerization of N ‐naphthyl aminobutynamide intermediate and subsequent intramolecular Ullmann‐type coupling reaction. This study clearly demonstrated the usefulness of coinage metal‐catalyzed cycloisomerization strategy in the construction of architecturally sophisticated pyridine‐fused heterocyclic scaffolds.

Journal of Heterocyclic Chemistry
Dankook University (KR)
National Research Foundation, Dankook University, National Research Foundation of Korea, Ministry of Science and ICT, South Korea
Sustainable cities and communities
Openalex Percentile: Top 89%
Catalytic C–H Functionalization Methods
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