{"title":"DMSO-K2S2O8介导的糖基C-3醚无碘转化为3-烯吡喃酮：呋喃[3,2-c]吡喃的合成","authors":"Bisma Rasool , Sanchari Kundu , Irshad Ahmad Zargar , Debaraj Mukherjee","doi":"10.1039/d4cc04278f","DOIUrl":null,"url":null,"abstract":"<div><div>A straightforward, highly efficient, and regioselective method for directly converting 3-<em>O</em>-benzylated and silylated glycals into their corresponding enones has been developed using a DMSO–K<sub>2</sub>S<sub>2</sub>O<sub>8</sub> reagent system. This reaction is scalable to gram quantities under mild conditions, achieving up to 80% yields. The resulting enones are valuable intermediates for the synthesis of furo[3,2-<em>c</em>] pyrans, which are integral components of various biologically significant scaffolds.</div></div>","PeriodicalId":67,"journal":{"name":"Chemical Communications","volume":"61 1","pages":"Pages 137-140"},"PeriodicalIF":4.2000,"publicationDate":"2024-12-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"DMSO–K2S2O8 mediated iodine-free conversion of glycal C-3 ether to 3-enopyranones: synthesis of furo[3,2-c] pyrans†\",\"authors\":\"Bisma Rasool , Sanchari Kundu , Irshad Ahmad Zargar , Debaraj Mukherjee\",\"doi\":\"10.1039/d4cc04278f\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>A straightforward, highly efficient, and regioselective method for directly converting 3-<em>O</em>-benzylated and silylated glycals into their corresponding enones has been developed using a DMSO–K<sub>2</sub>S<sub>2</sub>O<sub>8</sub> reagent system. This reaction is scalable to gram quantities under mild conditions, achieving up to 80% yields. The resulting enones are valuable intermediates for the synthesis of furo[3,2-<em>c</em>] pyrans, which are integral components of various biologically significant scaffolds.</div></div>\",\"PeriodicalId\":67,\"journal\":{\"name\":\"Chemical Communications\",\"volume\":\"61 1\",\"pages\":\"Pages 137-140\"},\"PeriodicalIF\":4.2000,\"publicationDate\":\"2024-12-02\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Chemical Communications\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/org/science/article/pii/S1359734524025783\",\"RegionNum\":2,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemical Communications","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1359734524025783","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
摘要
采用DMSO-K2S2O8试剂体系，建立了一种直接将3- o -苄基化和硅基化甘醛转化为相应烯酮的简单、高效和区域选择性的方法。该反应在温和条件下可扩展到克数，收率可达80%。所得到的烯酮是合成呋喃[3,2-c]吡喃的有价值的中间体，呋喃是各种具有重要生物学意义的支架的组成部分。
DMSO–K2S2O8 mediated iodine-free conversion of glycal C-3 ether to 3-enopyranones: synthesis of furo[3,2-c] pyrans†
A straightforward, highly efficient, and regioselective method for directly converting 3-O-benzylated and silylated glycals into their corresponding enones has been developed using a DMSO–K2S2O8 reagent system. This reaction is scalable to gram quantities under mild conditions, achieving up to 80% yields. The resulting enones are valuable intermediates for the synthesis of furo[3,2-c] pyrans, which are integral components of various biologically significant scaffolds.
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