Scalable synthesis of (±)-gregatin A via a 1,3-dipolar cycloaddition strategy†

IF 2.7 3区 化学 Q1 CHEMISTRY, ORGANIC Organic & Biomolecular Chemistry Pub Date : 2025-06-03 DOI:10.1039/d4ob02108h
Yiming Ding , Xiaoli Zhao , Chunlei Qu , Xianwen Long , Yaqiu Zhao , Jun Deng
{"title":"Scalable synthesis of (±)-gregatin A via a 1,3-dipolar cycloaddition strategy†","authors":"Yiming Ding ,&nbsp;Xiaoli Zhao ,&nbsp;Chunlei Qu ,&nbsp;Xianwen Long ,&nbsp;Yaqiu Zhao ,&nbsp;Jun Deng","doi":"10.1039/d4ob02108h","DOIUrl":null,"url":null,"abstract":"<div><div>A 6-step gram-scale synthesis of the fungal polyketide (±)-gregatin A is described. The synthetic route features an intermolecular 1,3-dipolar cycloaddition, a Mo-mediated disconnection of the isoxazole skeleton, and an acid-mediated deprotection/enamine hydrolysis and hemiketalization cascade.</div></div>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":"23 43","pages":"Pages 9819-9822"},"PeriodicalIF":2.7000,"publicationDate":"2025-06-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1477052025008225","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 6-step gram-scale synthesis of the fungal polyketide (±)-gregatin A is described. The synthetic route features an intermolecular 1,3-dipolar cycloaddition, a Mo-mediated disconnection of the isoxazole skeleton, and an acid-mediated deprotection/enamine hydrolysis and hemiketalization cascade.

Abstract Image

查看原文
分享 分享
微信好友 朋友圈 QQ好友 复制链接
本刊更多论文
1,3偶极环加成策略可扩展合成(±)-gregatin A。
描述了真菌聚酮(±)-gregatin A的6步克级合成。该合成路线具有分子间1,3-偶极环加成,mo介导的异恶唑骨架断开以及酸介导的脱保护/烯胺水解和半iketalization级联反应。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 去求助
来源期刊
Organic & Biomolecular Chemistry
Organic & Biomolecular Chemistry 化学-有机化学
CiteScore
5.50
自引率
9.40%
发文量
1056
审稿时长
1.3 months
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.
期刊最新文献
Bisaspochalasin F: a tetrahydrofuran ring-fused cytochalasan homodimer from an endophytic Aspergillus flavipes as a Cav3.2 inhibitor. Visible-light-induced C-H trifluoromethylation of several nitrogen heterocycles with CF3Br. Back cover B(C6F5)3/I2 co-mediated cascade [4 + 2]/[3 + 2] cyclization to access spiroimidazolines. Discovery of four novel furanosteroids and a new 4-methylprogesteroid from demethoxyviridin pathway-disrupted mutants of Nodulisporium sp. through cultivation time extension.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
现在去查看 取消
×
提示
确定
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
已复制链接
已复制链接
快去分享给好友吧!
我知道了
×
扫码分享
扫码分享
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:604180095
Book学术
文献互助 智能选刊 最新文献 互助须知 联系我们:info@booksci.cn
Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。
Copyright © 2023 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1