{"title":"Stereoselective synthesis of 3-oxo-2-<i>C</i>-branched glycosides from 2,3-unsaturated sugars <i>via</i> [3,3]-sigmatropic rearrangement.","authors":"Intzar Ali, Sravani Gundumalla, Ramu Sridhar Perali","doi":"10.1039/d4ob01769b","DOIUrl":null,"url":null,"abstract":"<p><p>A number of monosaccharide-derived glycals were initially converted to the corresponding 3-<i>O</i>-allyl 2,3-unsaturated glycosides and then subjected to Claisen rearrangement to produce 3-oxo-2-<i>C</i>-branched sugar derivatives with good to excellent stereoselectivity. The methodology was extended to synthesize allyl vinyl ethers derived from disaccharides. The application of the developed protocol was showcased by synthesizing the bicyclic core unit of the iridoid frameworks.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9000,"publicationDate":"2025-02-03","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/d4ob01769b","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
A number of monosaccharide-derived glycals were initially converted to the corresponding 3-O-allyl 2,3-unsaturated glycosides and then subjected to Claisen rearrangement to produce 3-oxo-2-C-branched sugar derivatives with good to excellent stereoselectivity. The methodology was extended to synthesize allyl vinyl ethers derived from disaccharides. The application of the developed protocol was showcased by synthesizing the bicyclic core unit of the iridoid frameworks.
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.
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