{"title":"Concise Synthesis of Azaphenanthrene Alkaloid Eupolauramine Via Au(I)-Catalyzed Cycloisomerization and Intramolecular Ullmann-Type Coupling Reaction","authors":"Eunyeong Kim, Young Taek Han","doi":"10.1002/jhet.4889","DOIUrl":null,"url":null,"abstract":"<div>\n \n <p>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 <i>N</i>-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.</p>\n </div>","PeriodicalId":194,"journal":{"name":"Journal of Heterocyclic Chemistry","volume":"61 10","pages":"1622-1626"},"PeriodicalIF":2.0000,"publicationDate":"2024-09-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Heterocyclic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/jhet.4889","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
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.
期刊介绍：
The Journal of Heterocyclic Chemistry is interested in publishing research on all aspects of heterocyclic chemistry, especially development and application of efficient synthetic methodologies and strategies for the synthesis of various heterocyclic compounds. In addition, Journal of Heterocyclic Chemistry promotes research in other areas that contribute to heterocyclic synthesis/application, such as synthesis design, reaction techniques, flow chemistry and continuous processing, multiphase catalysis, green chemistry, catalyst immobilization and recycling.
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