• 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

通过电化学环化全合成龙霉素A - C

Total Synthesis of Dragocins A-C through Electrochemical Cyclization.

作者信息

Smith Brendyn P, Truax Nathanyal J, Pollatos Alexandros S, Meanwell Michael, Bedekar Pranali, Garrido-Castro Alberto F, Baran Phil S

机构信息

Department of Chemistry, Scripps Research, 10550 N. Torrey Pines Road, La Jolla, California 92037, United States.

Department of Chemistry, University of Alberta, 11227 Saskatchewan Dr NW, Edmonton, AB T6G 2N4, Canada.

出版信息

Angew Chem Int Ed Engl. 2024 May 6;63(19):e202401107. doi: 10.1002/anie.202401107. Epub 2024 Mar 28.

DOI:10.1002/anie.202401107
PMID:38358802
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11619770/
Abstract

The first total synthesis of dragocins A-C, remarkable natural products containing an unusual C4' oxidized ribose architecture bridged by a polyhydroxylated pyrrolidine, is presented through a route featuring a number of uncommon maneuvers. Several generations towards the target molecules are presented, including the spectacular failure of a key C-H oxidation on a late-stage intermediate. The final route features rapid, stereocontrolled access to a densely functionalized pyrrolidine and an unprecedented diastereoselective oxidative electrochemical cyclization to forge the hallmark 9-membered ring. Preliminary studies suggest this electrochemical oxidation protocol is generally useful.

摘要

本文报道了dragoicins A-C的首次全合成，这是一类引人注目的天然产物，含有由多羟基化吡咯烷桥连的不寻常的C4'氧化核糖结构，合成路线采用了一系列不同寻常的操作。展示了向目标分子合成的几个阶段，包括后期中间体上关键的C-H氧化反应的惊人失败。最终路线的特点是能够快速、立体控制地合成一个高度官能化的吡咯烷，并通过前所未有的非对映选择性氧化电化学环化反应形成标志性的九元环。初步研究表明，这种电化学氧化方法具有普遍适用性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d214/11619770/9272118e2220/nihms-2037972-f0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d214/11619770/c951f5171147/nihms-2037972-f0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d214/11619770/335d0dab00be/nihms-2037972-f0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d214/11619770/9272118e2220/nihms-2037972-f0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d214/11619770/c951f5171147/nihms-2037972-f0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d214/11619770/335d0dab00be/nihms-2037972-f0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d214/11619770/9272118e2220/nihms-2037972-f0003.jpg

相似文献

1
Total Synthesis of Dragocins A-C through Electrochemical Cyclization.通过电化学环化全合成龙霉素A - C
Angew Chem Int Ed Engl. 2024 May 6;63(19):e202401107. doi: 10.1002/anie.202401107. Epub 2024 Mar 28.
2
Synthesis of Three-Dimensionally Fascinating Diterpenoid Alkaloids and Related Diterpenes.三维迷人的二萜生物碱和相关二萜的合成。
Acc Chem Res. 2021 Jan 5;54(1):22-34. doi: 10.1021/acs.accounts.0c00720. Epub 2020 Dec 22.
3
Total synthesis of (+)-sarain A.(+)-沙林 A 的全合成。
J Am Chem Soc. 2007 Oct 3;129(39):11987-2002. doi: 10.1021/ja074300t. Epub 2007 Sep 12.
4
Total Synthesis of (-)-Voacinol and (-)-Voacandimine C.(-)-Voacinol 和 (-)-Voacandimine C 的全合成。
J Am Chem Soc. 2022 May 25;144(20):9126-9131. doi: 10.1021/jacs.2c03057. Epub 2022 May 11.
5
Formal Synthesis of Sarain A: Intramolecular Cycloaddition of an Eight-Membered Cyclic Nitrone to Construct the 2-Azabicyclo[3.3.1]nonane Framework.Sarain A 的全合成：八元环氮氧化物的分子内环加成反应构建 2-氮杂双环[3.3.1]壬烷骨架。
Angew Chem Int Ed Engl. 2015 Jun 15;54(25):7367-70. doi: 10.1002/anie.201501633. Epub 2015 May 8.
6
Total Synthesis of (-)-Pepluanol B: Conformational Control of the Eight-Membered-Ring System.（-）-佩普卢醇B的全合成：八元环体系的构象控制
Angew Chem Int Ed Engl. 2020 Mar 2;59(10):3966-3970. doi: 10.1002/anie.201915876. Epub 2020 Jan 29.
7
A Divergent Synthetic Route to the Vallesamidine and Schizozygine Alkaloids: Total Synthesis of (+)-Vallesamidine and (+)-14,15-Dehydrostrempeliopine.一种瓦来萨米定和施哲西嗪生物碱的发散性综合路径：(+)-瓦来萨米定和 (+)-14,15-去氢施氏紫堇碱的全合成。
Angew Chem Int Ed Engl. 2019 Dec 9;58(50):18040-18045. doi: 10.1002/anie.201910593. Epub 2019 Oct 30.
8
In Pursuit of Synthetic Efficiency: Convergent Approaches.追求合成效率：汇聚方法。
Acc Chem Res. 2021 Feb 2;54(3):569-582. doi: 10.1021/acs.accounts.0c00727. Epub 2021 Jan 15.
9
Discovery and Surprises with Cyclizations, Cycloadditions, Fragmentations, and Rearrangements in Complex Settings.在复杂环境下的环化、环加成、碎裂和重排反应中的发现和惊喜。
Acc Chem Res. 2021 Feb 16;54(4):890-902. doi: 10.1021/acs.accounts.0c00814. Epub 2021 Feb 3.
10
Enantioselective construction of a polyhydroxylated pyrrolidine skeleton from 3-vinylaziridine-2-carboxylates: synthesis of (+)-DMDP and a potential common intermediate for (+)-hyacinthacine A1 and (+)-1-epi-australine.从 3-乙烯基氮丙啶-2-羧酸酯中对映选择性构建多羟基化吡咯烷骨架：（+）-DMDP 的合成及（+）-海葱甲素 A1 和（+）-1-表-澳洲茄碱的潜在通用中间体。
J Org Chem. 2012 Sep 21;77(18):7988-99. doi: 10.1021/jo301178b. Epub 2012 Sep 5.

引用本文的文献

1
Asymmetric C-H Functionalization of -Boc-2,5-dihydro-1-pyrrole and Its Application as a Key Step in the Synthesis of (-)-Dragocin D.-叔丁氧羰基-2,5-二氢-1-吡咯的不对称C-H官能化及其作为(-)-龙脑香素D合成关键步骤的应用
J Am Chem Soc. 2025 Aug 6;147(31):28098-28106. doi: 10.1021/jacs.5c08080. Epub 2025 Jul 28.
2
Response of reaction mechanisms to electric-field catalysis on carbon nanotubes in microfluidic reactors.微流控反应器中碳纳米管上反应机理对电场催化的响应
Chem Sci. 2025 May 28. doi: 10.1039/d5sc02934a.
3
Electric-Field Catalysis on Carbon Nanotubes in Electromicrofluidic Reactors: Monoterpene Cyclizations.电微流体反应器中碳纳米管上的电场催化：单萜环化反应
Angew Chem Int Ed Engl. 2025 Jan 21;64(4):e202417333. doi: 10.1002/anie.202417333. Epub 2024 Nov 14.

本文引用的文献

1
Scalable Electrochemical Decarboxylative Olefination Driven by Alternating Polarity.由交替极性驱动的可扩展电化学脱羧烯基化反应
Angew Chem Int Ed Engl. 2023 Oct 16;62(42):e202309157. doi: 10.1002/anie.202309157. Epub 2023 Sep 13.
2
Photochemical Synthesis of the Bioactive Fragment of Salbutamol and Derivatives in a Self-Optimizing Flow Chemistry Platform.在自优化流动化学平台中光化学合成沙丁胺醇生物活性片段及其衍生物。
Chemistry. 2022 Aug 1;28(43):e202201385. doi: 10.1002/chem.202201385. Epub 2022 Jun 8.
3
Chemoselective (Hetero)Arene Electroreduction Enabled by Rapid Alternating Polarity.快速交替极性实现的（杂）芳环化学选择性电还原。
J Am Chem Soc. 2022 Apr 6;144(13):5762-5768. doi: 10.1021/jacs.2c02102. Epub 2022 Mar 29.
4
Chemoselective Electrosynthesis Using Rapid Alternating Polarity.快速交替极性的选择性电合成。
J Am Chem Soc. 2021 Oct 13;143(40):16580-16588. doi: 10.1021/jacs.1c06572. Epub 2021 Oct 1.
5
Decarboxylative Halogenation of Organic Compounds.有机化合物的脱羧卤化反应。
Chem Rev. 2021 Jan 13;121(1):412-484. doi: 10.1021/acs.chemrev.0c00813. Epub 2020 Nov 17.
6
Construction of Medium-Sized Rings by Gold Catalysis.金催化构建中型环
Chem Rev. 2021 Jul 28;121(14):8926-8947. doi: 10.1021/acs.chemrev.0c00793. Epub 2020 Oct 6.
7
Total Synthesis of the Putative Structure of Asperipin-2a and Stereochemical Reassignment. Asperipin-2a 的假定结构的全合成及立体化学重排。
Org Lett. 2020 Oct 2;22(19):7730-7734. doi: 10.1021/acs.orglett.0c02884. Epub 2020 Sep 22.
8
Synthesis and hetero-Diels-Alder reactions of enantiomerically pure dihydro-1-azepines.对映体纯二氢-1-氮杂环庚烷的合成及杂环狄尔斯-阿尔德反应
Chem Commun (Camb). 2020 Aug 25;56(68):9803-9806. doi: 10.1039/d0cc04413j.
9
Electrochemical oxidation-induced etherification via C(sp)─H/O─H cross-coupling.电化学氧化诱导的通过C(sp)─H/O─H交叉偶联实现的醚化反应。
Sci Adv. 2020 May 15;6(20):eaaz0590. doi: 10.1126/sciadv.aaz0590. eCollection 2020 May.
10
A common strategy towards the synthesis of 1,4-dideoxy-1,4-imino-l-xylitol, deacetyl (+)-anisomycin and amino-substituted piperidine iminosugars.一种合成 1,4-二脱氧-1,4-亚氨基-L-木糖醇、去乙酰基（+）-茴香霉素和氨基取代哌啶亚氨基糖的常见策略。
Carbohydr Res. 2020 Jun;492:107988. doi: 10.1016/j.carres.2020.107988. Epub 2020 Mar 25.