• 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

通过金属-卤素交换环化反应高效全合成脱氢白藜芦醇。

Efficient total synthesis of dehydro--viniferin through metal-halogen exchange cyclization.

作者信息

Cao Jinfang, Zhu Qibin, Sha Zhen, Zhou Xiaoxuan, Zhu Ruitong, Yao Chunsuo

机构信息

State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences, Peking Union Medical College Beijing 100050 P. R. China

出版信息

RSC Adv. 2025 Mar 11;15(10):7738-7741. doi: 10.1039/d5ra00960j. eCollection 2025 Mar 6.

DOI:10.1039/d5ra00960j
PMID:40070388
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11895512/
Abstract

Bioactive dehydro--viniferin was synthesized through an efficient and practical eight-step route, achieving an overall yield of 27%. The synthesis process involves an intramolecular cyclization and dehalogenation a metal-halogen exchange, producing 3-arylbenzofuran, with the di-iodinated -aryloxyketone serving as the key intermediate. Long reaction times and the use of excess reagent -PrMgCl·LiCl facilitate metal-halogen exchange cyclization and dehalogenation. This synthetic approach, scalable for the production of analogs, was successfully conducted for the first time in multigram quantities.

摘要

通过一条高效实用的八步路线合成了具有生物活性的脱氢白藜芦醇，总产率达到27%。合成过程涉及分子内环化和脱卤反应——一种金属-卤素交换反应，生成3-芳基苯并呋喃，其中二碘化芳氧基酮作为关键中间体。较长的反应时间以及使用过量试剂异丙基氯化镁·氯化锂有助于金属-卤素交换环化和脱卤反应。这种可扩展用于生产类似物的合成方法首次成功地以多克量规模进行。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6c45/11895512/8fd80429bbf3/d5ra00960j-s6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6c45/11895512/bedd37d68f1e/d5ra00960j-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6c45/11895512/c814c491135b/d5ra00960j-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6c45/11895512/c03725d66788/d5ra00960j-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6c45/11895512/7b237d8ce469/d5ra00960j-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6c45/11895512/05376477b80d/d5ra00960j-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6c45/11895512/332246908f21/d5ra00960j-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6c45/11895512/8fd80429bbf3/d5ra00960j-s6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6c45/11895512/bedd37d68f1e/d5ra00960j-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6c45/11895512/c814c491135b/d5ra00960j-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6c45/11895512/c03725d66788/d5ra00960j-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6c45/11895512/7b237d8ce469/d5ra00960j-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6c45/11895512/05376477b80d/d5ra00960j-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6c45/11895512/332246908f21/d5ra00960j-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/6c45/11895512/8fd80429bbf3/d5ra00960j-s6.jpg

相似文献

1
Efficient total synthesis of dehydro--viniferin through metal-halogen exchange cyclization.通过金属-卤素交换环化反应高效全合成脱氢白藜芦醇。
RSC Adv. 2025 Mar 11;15(10):7738-7741. doi: 10.1039/d5ra00960j. eCollection 2025 Mar 6.
2
Total synthesis of the active resveratrol dimer dehydro--viniferin.活性白藜芦醇二聚体脱氢白藜芦醇的全合成。
J Asian Nat Prod Res. 2020 Oct;22(10):947-955. doi: 10.1080/10286020.2020.1776267. Epub 2020 Jun 22.
3
Recent Advances in Halogen-Metal Exchange Reactions.卤代金属交换反应的最新进展
Acc Chem Res. 2024 Jul 16;57(14):1951-1963. doi: 10.1021/acs.accounts.4c00242. Epub 2024 Jul 2.
4
A concise and efficient total synthetic route of active stilbene dimer (±)--viniferin.一种简洁高效的活性芪二聚体（±）-葡萄素的全合成路线。
RSC Adv. 2022 Apr 8;12(18):11100-11103. doi: 10.1039/d2ra01385a. eCollection 2022 Apr 7.
5
Total synthesis of diptoindonesin G via a highly efficient domino cyclodehydration/intramolecular Friedel-Crafts acylation/regioselective demethylation sequence.通过高效的串联环脱水/分子内傅克酰化/区域选择性脱甲基序列，全合成二肽吲哚宁 G。
Org Lett. 2010 Nov 19;12(22):5314-7. doi: 10.1021/ol102322g. Epub 2010 Oct 29.
6
Total synthesis of (±)-20S-hydroxy-1,2-dehydro-pseudoaspidospermidine via a C-H activation/transannular cyclization strategy.
Chem Commun (Camb). 2017 Jul 4;53(54):7451-7453. doi: 10.1039/c7cc02699d.
7
Halogen-Induced Controllable Cyclizations as Diverse Heterocycle Synthetic Strategy.卤素诱导的可控环化反应作为一种多样化杂环合成策略。
Molecules. 2020 Dec 18;25(24):6007. doi: 10.3390/molecules25246007.
8
Halogen-Metal Exchange on Bromoheterocyclics with Substituents Containing an Acidic Proton via Formation of a Magnesium Intermediate.通过形成镁中间体，在含酸性质子的取代基溴杂环上进行卤-金属交换。
Molecules. 2017 Nov 11;22(11):1952. doi: 10.3390/molecules22111952.
9
Asymmetric synthesis of 1,2,9,9a-tetrahydrocyclopropa[c]benzo[e]indol-4-one (CBI).1,2,9,9a-四氢环丙[c]苯并[e]吲哚-4-酮（CBI）的不对称合成。
J Org Chem. 2011 Jan 21;76(2):583-7. doi: 10.1021/jo102136w. Epub 2010 Dec 30.
10
Metalation vs Nucleophilic Addition in the Reactions of N-Phenethylimides with Organolithium Reagents. Ready Access to Isoquinoline Derivatives via N-Acyliminium Ions and Parham-Type Cyclizations.N-苯乙基亚胺与有机锂试剂反应中的金属化与亲核加成。通过N-酰基亚胺离子和帕尔哈姆型环化反应便捷合成异喹啉衍生物。
J Org Chem. 1997 Apr 4;62(7):2080-2092. doi: 10.1021/jo962155o.

本文引用的文献

1
A concise and efficient total synthetic route of active stilbene dimer (±)--viniferin.一种简洁高效的活性芪二聚体（±）-葡萄素的全合成路线。
RSC Adv. 2022 Apr 8;12(18):11100-11103. doi: 10.1039/d2ra01385a. eCollection 2022 Apr 7.
2
Total synthesis of the active resveratrol dimer dehydro--viniferin.活性白藜芦醇二聚体脱氢白藜芦醇的全合成。
J Asian Nat Prod Res. 2020 Oct;22(10):947-955. doi: 10.1080/10286020.2020.1776267. Epub 2020 Jun 22.
3
Exploring resveratrol dimers as virulence blocking agents - Attenuation of type III secretion in Yersinia pseudotuberculosis and Pseudomonas aeruginosa.
探索白藜芦醇二聚体作为毒力阻断剂 - 减弱假结核耶尔森氏菌和铜绿假单胞菌的 III 型分泌系统。
Sci Rep. 2020 Feb 7;10(1):2103. doi: 10.1038/s41598-020-58872-0.
4
Antimicrobial activity of resveratrol-derived monomers and dimers against foodborne pathogens.白藜芦醇单体和二聚体对食源性病原体的抗菌活性。
Sci Rep. 2019 Dec 20;9(1):19525. doi: 10.1038/s41598-019-55975-1.
5
Total Synthesis of (±)-Pestalachloride C and (±)-Pestalachloride D through a Biomimetic Knoevenagel/Hetero-Diels-Alder Cascade.通过仿生克诺文纳格尔/杂环狄尔斯-阿尔德串联反应全合成（±）-Pestalachloride C和（±）-Pestalachloride D
Org Lett. 2019 Mar 15;21(6):1755-1759. doi: 10.1021/acs.orglett.9b00323. Epub 2019 Mar 5.
6
Total Synthesis of Viniferifuran, Resveratrol-Piceatannol Hybrid, Anigopreissin A and Analogues - Investigation of Demethylation Strategies.葡萄呋喃、白藜芦醇-白皮杉醇杂合物、山姜素A及其类似物的全合成——去甲基化策略研究
Adv Synth Catal. 2016 Dec 22;358(24):4085-4092. doi: 10.1002/adsc.201601089. Epub 2016 Dec 8.
7
Naturally active oligostilbenes.天然活性低聚芪类化合物。
J Asian Nat Prod Res. 2016;18(4):376-407. doi: 10.1080/10286020.2015.1094464. Epub 2015 Dec 21.
8
Chemistry and Biology of Resveratrol-Derived Natural Products.白藜芦醇衍生天然产物的化学与生物学
Chem Rev. 2015 Sep 9;115(17):8976-9027. doi: 10.1021/cr500689b. Epub 2015 Apr 2.
9
Enantioselective intramolecular C-H insertion reactions of donor-donor metal carbenoids.供体-供体金属卡宾的对映选择性分子内C-H插入反应
J Am Chem Soc. 2014 Oct 29;136(43):15142-5. doi: 10.1021/ja508586t. Epub 2014 Oct 21.
10
Natural stilbenoids: distribution in the plant kingdom and chemotaxonomic interest in Vitaceae.天然芪类化合物：在植物界的分布及在葡萄科中的化学分类学意义。
Nat Prod Rep. 2012 Nov;29(11):1317-33. doi: 10.1039/c2np20049j.