• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利：CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法，用中文像聊天一样搜索，搜遍4000万医学文献。AI智能推荐，让科研检索更轻松。

立即免费搜索

文件翻译

保留排版，准确专业，支持PDF/Word/PPT等文件格式，支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述，25分钟生成高质量综述，智能提取关键信息，辅助科研写作。

立即免费体验

远程立体诱导分子内腈氧化物环加成反应：(-)-11β-羟基弯孢霉菌素的不对称全合成及结构修正

Remote Stereoinductive Intramolecular Nitrile Oxide Cycloaddition: Asymmetric Total Synthesis and Structure Revision of (-)-11β-Hydroxycurvularin.

作者信息

Choe Hyeonjeong, Pham Thuy Trang, Lee Joo Yun, Latif Muhammad, Park Haeil, Kang Young Kee, Lee Jongkook

机构信息

Drug Discovery Division, Korea Research Institute of Chemical Technology , Yuseong, Daejeon 34114, Republic of Korea.

College of Pharmacy, Kangwon National University , 1 Kangwondaehak-gil, Chuncheon, Gangwon-do 24341, Republic of Korea.

出版信息

J Org Chem. 2016 Mar 18;81(6):2612-7. doi: 10.1021/acs.joc.5b02760. Epub 2016 Feb 29.

DOI:10.1021/acs.joc.5b02760
PMID:26894643
Abstract

The first total synthesis and structure revision of (-)-11β-hydroxycurvularin (1b), a macrolide possessing a β-hydroxyketone moiety, were accomplished. The β-hydroxyketone moiety in this natural product was introduced by cleavage of the N-O bond in an isoxazoline ring that was formed diastereoselectively in a 1,5-remote stereocontrolled fashion by employing intramolecular nitrile oxide cycloaddition.

摘要

完成了具有β - 羟基酮部分的大环内酯（-）-11β - 羟基弯孢霉菌素（1b）的首次全合成及结构修正。该天然产物中的β - 羟基酮部分是通过异恶唑啉环中N - O键的断裂引入的，而异恶唑啉环是通过分子内腈氧化物环加成以1,5 - 远程立体控制方式非对映选择性地形成的。

相似文献

1
Remote Stereoinductive Intramolecular Nitrile Oxide Cycloaddition: Asymmetric Total Synthesis and Structure Revision of (-)-11β-Hydroxycurvularin.远程立体诱导分子内腈氧化物环加成反应：(-)-11β-羟基弯孢霉菌素的不对称全合成及结构修正
J Org Chem. 2016 Mar 18;81(6):2612-7. doi: 10.1021/acs.joc.5b02760. Epub 2016 Feb 29.
2
Highly regio- and diastereoselective, acidic clay supported intramolecular nitrile oxide-alkene cycloaddition on D-ribose derived nitriles: an efficient synthetic route to isoxazoline fused five and six membered carbocycles.高度区域和非对映选择性的、酸性粘土负载的D-核糖衍生腈的分子内腈氧化物-烯烃环加成反应：一种合成异恶唑啉稠合五元及六元碳环的有效方法。
Carbohydr Res. 2014 Oct 29;398:13-8. doi: 10.1016/j.carres.2014.06.007. Epub 2014 Jun 19.
3
Synthesis of Bicyclic Isoxazoles and Isoxazolines via Intramolecular Nitrile Oxide Cycloaddition.通过分子内腈氧化物环加成合成双环异恶唑和异恶唑啉
Molecules. 2015 Jun 12;20(6):10910-27. doi: 10.3390/molecules200610910.
4
A novel protocol for the facile construction of tetrahydroquinoline fused tricyclic frameworks via an intramolecular 1,3-dipolar nitrile oxide cycloaddition reaction.一种通过分子内1,3-偶极腈氧化物环加成反应简便构建四氢喹啉稠合三环骨架的新方法。
Org Biomol Chem. 2015 Oct 21;13(39):10007-14. doi: 10.1039/c5ob01060h.
5
Synthesis and intramolecular nitrile oxide cycloaddition of 3,5'-ether-linked pseudooligosaccharide derivatives: an approach to chiral macrooxacycles.3,5'-醚键连接的假寡糖衍生物的合成及分子内腈氧化物环加成反应：一种制备手性大环氧杂环的方法。
J Org Chem. 2005 Oct 14;70(21):8579-82. doi: 10.1021/jo050689w.
6
Regio- and stereoselective access to novel ring-condensed steroidal isoxazolines.区域和立体选择性合成新型稠环甾体异恶唑啉。
Steroids. 2014 Sep;87:76-85. doi: 10.1016/j.steroids.2014.05.019. Epub 2014 Jun 10.
7
First total syntheses and spectral data corrections of 11-alpha-methoxycurvularin and 11-beta-methoxycurvularin.11-α-甲氧基弯孢霉菌素和11-β-甲氧基弯孢霉菌素的首次全合成及光谱数据校正
J Org Chem. 2007 Dec 7;72(25):9846-9. doi: 10.1021/jo701885n. Epub 2007 Nov 8.
8
A modular approach to polyketide building blocks: cycloadditions of nitrile oxides and homoallylic alcohols.聚酮化合物构建模块的模块化方法：腈氧化物与高烯丙醇的环加成反应
Org Lett. 2005 May 12;7(10):2011-4. doi: 10.1021/ol0504953.
9
Investigation into the regiochemistry of some isoxazoles derived from 1,3-dipolar cycloaddition of 4-nitrobenzonitrile oxide with some dipolarophiles: a combined theoretical and experimental studies.关于 4-硝基苯甲腈氧化物与某些偶极子 1,3-偶极环加成反应生成的一些异恶唑的区域化学研究：理论与实验研究的结合。
Spectrochim Acta A Mol Biomol Spectrosc. 2011 Sep;79(5):1375-80. doi: 10.1016/j.saa.2011.04.071. Epub 2011 May 19.
10
Synthesis of isoxazoles by hypervalent iodine-induced cycloaddition of nitrile oxides to alkynes.通过高价碘诱导的腈氧化物与炔烃的环加成反应合成异恶唑。
Chem Commun (Camb). 2011 Mar 21;47(11):3198-200. doi: 10.1039/c0cc04646a. Epub 2011 Feb 1.

引用本文的文献

1
Study on Nitrile Oxide for Low-Temperature Curing of Liquid Polybutadiene.用于液态聚丁二烯低温固化的氮氧化物研究。
Materials (Basel). 2022 May 9;15(9):3396. doi: 10.3390/ma15093396.
2
Chemoenzymatic Dynamic Kinetic Asymmetric Transformations of β-Hydroxyketones.β-羟基酮的酶促动态动力学不对称转化。
Chemistry. 2021 Nov 11;27(63):15623-15627. doi: 10.1002/chem.202102683. Epub 2021 Oct 5.
3
3-Benzoylisoxazolines by 1,3-Dipolar Cycloaddition: Chloramine-T-Catalyzed Condensation of α-Nitroketones with Dipolarophiles.3-苯甲酰基异恶唑啉的 1,3-偶极环加成反应：氯胺-T 催化的α-硝基酮与偶极子的缩合反应。
Molecules. 2021 Jun 8;26(12):3491. doi: 10.3390/molecules26123491.
4
Unconventional Macrocyclizations in Natural Product Synthesis.天然产物合成中的非常规大环化反应
ACS Cent Sci. 2020 Nov 25;6(11):1869-1889. doi: 10.1021/acscentsci.0c00599. Epub 2020 Sep 21.
5
Crystal structure of 5-(4--but-oxy-phen-yl)-3-(4--octyloxyphen-yl)-4,5-di-hydro-isoxazole.5-（4-丁氧基苯基）-3-（4-辛氧基苯基）-4,5-二氢异恶唑的晶体结构
Acta Crystallogr E Crystallogr Commun. 2019 May 24;75(Pt 6):896-899. doi: 10.1107/S2056989019007412. eCollection 2019 Jun 1.
6
Recent Advances in Substrate-Controlled Asymmetric Cyclization for Natural Product Synthesis.用于天然产物合成的底物控制不对称环化反应的最新进展
Molecules. 2017 Jun 26;22(7):1069. doi: 10.3390/molecules22071069.