{"title":"Concise asymmetric synthesis of (-)-Bao Gong Teng A <i>via</i> Evans chiral auxiliary-based 1,3-dipolar cycloaddition.","authors":"Yi-Wen Zhao, Jun-Fei Wang, Jianrong Xu, Hongzhuan Chen, Yun-Xuan Tan, Ping Tian","doi":"10.1039/d5ob00014a","DOIUrl":null,"url":null,"abstract":"<p><p>We present a concise asymmetric synthesis of (-)-Bao Gong Teng A, a 2-hydroxylated tropane alkaloid with hypotensive and miotic activities isolated from the Chinese herb <i>Erycibe obtusifolia</i> Benth. Using an Evans chiral auxiliary, we achieve a regio- and stereoselective 1,3-dipolar cycloaddition between <i>p</i>-chlorobenzyl pyridinium salt and (<i>R</i>)-3-acryloyl-4-phenyloxazolidin-2-one, efficiently generating the tropane skeleton on a decagram scale. This methodology provides a rapid and practical synthesis of optically active (-)-Bao Gong Teng A for further biological studies.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9000,"publicationDate":"2025-02-06","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/d5ob00014a","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 concise asymmetric synthesis of (-)-Bao Gong Teng A, a 2-hydroxylated tropane alkaloid with hypotensive and miotic activities isolated from the Chinese herb Erycibe obtusifolia Benth. Using an Evans chiral auxiliary, we achieve a regio- and stereoselective 1,3-dipolar cycloaddition between p-chlorobenzyl pyridinium salt and (R)-3-acryloyl-4-phenyloxazolidin-2-one, efficiently generating the tropane skeleton on a decagram scale. This methodology provides a rapid and practical synthesis of optically active (-)-Bao Gong Teng A for further biological studies.
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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