{"title":"亚氨基糖c -香豆素苷直接合成顺式双环γ-内酰胺衍生物","authors":"Likai Zhou, Lijing Feng, Jilai Wu, Chao Wei, Hua Chen","doi":"10.1021/acs.orglett.5c01201","DOIUrl":null,"url":null,"abstract":"A simple and effective synthesis method has been developed through Mannich and transannular reaction mechanisms to convert iminosugar <i>C</i>-coumarinyl glycosides <b>4a</b> into <i>cis</i>-bicyclic γ-lactam derivatives <b>8a</b>. The adaptability of this method has been demonstrated through various substituted coumarins, tosylated sugars, and amines. The extension reaction proved the plasticity of the bicyclic skeleton. In addition, this reaction has the characteristics of simple operation, a high yield, and high atomic economy.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"41 1","pages":""},"PeriodicalIF":5.0000,"publicationDate":"2025-05-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Direct Synthesis of cis-Bicyclic γ-Lactam Derivatives from Iminosugar C-Coumarinyl Glycosides\",\"authors\":\"Likai Zhou, Lijing Feng, Jilai Wu, Chao Wei, Hua Chen\",\"doi\":\"10.1021/acs.orglett.5c01201\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"A simple and effective synthesis method has been developed through Mannich and transannular reaction mechanisms to convert iminosugar <i>C</i>-coumarinyl glycosides <b>4a</b> into <i>cis</i>-bicyclic γ-lactam derivatives <b>8a</b>. The adaptability of this method has been demonstrated through various substituted coumarins, tosylated sugars, and amines. The extension reaction proved the plasticity of the bicyclic skeleton. In addition, this reaction has the characteristics of simple operation, a high yield, and high atomic economy.\",\"PeriodicalId\":54,\"journal\":{\"name\":\"Organic Letters\",\"volume\":\"41 1\",\"pages\":\"\"},\"PeriodicalIF\":5.0000,\"publicationDate\":\"2025-05-30\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1021/acs.orglett.5c01201\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.5c01201","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
Direct Synthesis of cis-Bicyclic γ-Lactam Derivatives from Iminosugar C-Coumarinyl Glycosides
A simple and effective synthesis method has been developed through Mannich and transannular reaction mechanisms to convert iminosugar C-coumarinyl glycosides 4a into cis-bicyclic γ-lactam derivatives 8a. The adaptability of this method has been demonstrated through various substituted coumarins, tosylated sugars, and amines. The extension reaction proved the plasticity of the bicyclic skeleton. In addition, this reaction has the characteristics of simple operation, a high yield, and high atomic economy.
期刊介绍:
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.