{"title":"Synthesis of the polymethoxyflavones nobiletin, tangeretin, isosinensetin, and gardenin A-D.","authors":"Cheng-Hang Liu, Mengyang Xu, Jianke Du, Yang Ni, Qiyun Luo, Ziyan Wang, Wenyue Tan, Yunfang He, Linrun Zhang, Xiaodong Jia, Xingzeng Zhao","doi":"10.1039/d5ob00097a","DOIUrl":null,"url":null,"abstract":"<p><p>We present a practical synthesis of 2'-hydroxy-3',4',5',6'-tetramethoxyacetophenone, a multi-substituted benzene derivative, <i>via</i> CuCl-catalyzed Ullmann-type coupling reaction with MeONa. 2'-Hydroxy-3',4',5',6'-tetramethoxyacetophenone is the key intermediate for the total synthesis of various polymethoxyflavones. Subsequently, nobiletin, tangeretin, and gardenin A-D, are synthesized from this intermediate.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9000,"publicationDate":"2025-02-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d5ob00097a","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
We present a practical synthesis of 2'-hydroxy-3',4',5',6'-tetramethoxyacetophenone, a multi-substituted benzene derivative, via CuCl-catalyzed Ullmann-type coupling reaction with MeONa. 2'-Hydroxy-3',4',5',6'-tetramethoxyacetophenone is the key intermediate for the total synthesis of various polymethoxyflavones. Subsequently, nobiletin, tangeretin, and gardenin A-D, are synthesized from this intermediate.
期刊介绍:
Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.