{"title":"Synthesis of (±)-Entecavir","authors":"Z. R. Valiullina, N. A. Ivanova, M. S. Miftakhov","doi":"10.1134/S1070428024030060","DOIUrl":null,"url":null,"abstract":"<p>A practical synthesis of (±)-entecavir has been developed on the basis of Corey (±)-lactone diol. The key stage is the synthesis of (1<i>R</i>*,3<i>R</i>*,4<i>S</i>*)-4-(1-ethoxyethoxy)-3-[(1-ethoxyethoxy)methyl]-2-methylidenecyclopentan-1-ol by oxidative decarboxylation of 2-{(1<i>S</i>*,2<i>R</i>*,3<i>S</i>*,5<i>R</i>*)-5-{[<i>tert</i>-butyl(dimethyl)silyl]oxy}-3-(1-ethoxyethoxy)-2-[(1-ethoxyethoxy)methyl]cyclopentyl}acetic acid with lead tetraacetate.</p>","PeriodicalId":766,"journal":{"name":"Russian Journal of Organic Chemistry","volume":"60 3","pages":"410 - 414"},"PeriodicalIF":0.8000,"publicationDate":"2024-05-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Russian Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1134/S1070428024030060","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
A practical synthesis of (±)-entecavir has been developed on the basis of Corey (±)-lactone diol. The key stage is the synthesis of (1R*,3R*,4S*)-4-(1-ethoxyethoxy)-3-[(1-ethoxyethoxy)methyl]-2-methylidenecyclopentan-1-ol by oxidative decarboxylation of 2-{(1S*,2R*,3S*,5R*)-5-{[tert-butyl(dimethyl)silyl]oxy}-3-(1-ethoxyethoxy)-2-[(1-ethoxyethoxy)methyl]cyclopentyl}acetic acid with lead tetraacetate.
期刊介绍：
Russian Journal of Organic Chemistry is an international peer reviewed journal that covers all aspects of modern organic chemistry including organic synthesis, theoretical organic chemistry, structure and mechanism, and the application of organometallic compounds in organic synthesis.
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