• 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

(+)-卷柏双黄酮B报道结构的仿生全合成。

Biomimetic total synthesis of the reported structure of (+)-selaginedorffone B.

作者信息

Kundu Sourav, Jana Debgopal, Mandal Nilangshu, Mondal Ayan, Murmu Ranjit, Roy Nanda Kishore, Datta Ayan, Bisai Alakesh

机构信息

Department of Chemistry, Indian Institute of Science Education and Research Bhopal Bhopal Bypass Road Bhopal 462 066 Madhya Pradesh India

Department of Chemistry, Indian Institute of Science Education and Research Kolkata Mohanpur Campus, Nadia Kalyani 741 246 West Bengal India.

出版信息

Chem Sci. 2024 Jul 25;15(36):14946-53. doi: 10.1039/d4sc04103h.

DOI:10.1039/d4sc04103h
PMID:39246359
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11376052/
Abstract

The first enantioselective total synthesis of the reported structure of the structurally unique aromatic tetraterpenoid of anti-cancer potential, (+)-selaginedorffone B (2), has been accomplished from two modified abietane diterpenoids through an intermolecular Diels-Alder reaction between a bio-inspired diene 3 (HOMO counterpart) and dienophile 4 (corresponding LUMO counterpart) in a 23-step sequence, whereas the core framework of the monomeric abietane diterpenoid was constructed alkyne-activated ene-cyclization. Computational analysis was conducted to reveal the intricate regio and diastereoselectivity of this novel Diels-Alder reaction, strengthening the experimental results. The absolute configuration of the synthesized molecule was validated through X-ray studies of late-stage intermediates as well as comprehensive 2D NMR analysis.

摘要

通过一种结构独特的具有抗癌潜力的芳香族四萜类化合物（+）-卷柏双黄酮B（2）的报道结构的首次对映选择性全合成，是由两种修饰的枞酸型二萜通过生物启发的二烯3（最高占据分子轨道对应物）和亲双烯体4（相应的最低未占分子轨道对应物）之间的分子间狄尔斯-阿尔德反应，以23步序列完成的，而单体枞酸型二萜的核心骨架是通过炔烃活化的烯环化构建的。进行了计算分析以揭示这种新型狄尔斯-阿尔德反应复杂的区域和非对映选择性，从而强化了实验结果。通过对后期中间体的X射线研究以及全面的二维核磁共振分析，验证了合成分子的绝对构型。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/91bd/11410089/3461c44e1464/d4sc04103h-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/91bd/11410089/201f6d1f138e/d4sc04103h-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/91bd/11410089/65126e8fb55f/d4sc04103h-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/91bd/11410089/bed3ac7e0c2d/d4sc04103h-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/91bd/11410089/a36387152ae1/d4sc04103h-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/91bd/11410089/bf50f83b204e/d4sc04103h-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/91bd/11410089/8f583cbfc859/d4sc04103h-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/91bd/11410089/3461c44e1464/d4sc04103h-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/91bd/11410089/201f6d1f138e/d4sc04103h-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/91bd/11410089/65126e8fb55f/d4sc04103h-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/91bd/11410089/bed3ac7e0c2d/d4sc04103h-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/91bd/11410089/a36387152ae1/d4sc04103h-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/91bd/11410089/bf50f83b204e/d4sc04103h-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/91bd/11410089/8f583cbfc859/d4sc04103h-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/91bd/11410089/3461c44e1464/d4sc04103h-s4.jpg

相似文献

1
Biomimetic total synthesis of the reported structure of (+)-selaginedorffone B.(+)-卷柏双黄酮B报道结构的仿生全合成。
Chem Sci. 2024 Jul 25;15(36):14946-53. doi: 10.1039/d4sc04103h.
2
Modified Abietane Diterpenoids from Whole Plants of Selaginella moellendorffii.卷柏全草中的改性枞型二萜。
J Nat Prod. 2018 Feb 23;81(2):418-422. doi: 10.1021/acs.jnatprod.7b00909. Epub 2018 Feb 7.
3
Catalytic enantioselective aza-Diels-alder reactions of imines--an approach to optically active nonproteinogenic alpha-amino acids.亚胺的催化对映选择性氮杂狄尔斯-阿尔德反应——一种合成光学活性非蛋白质ogenicα-氨基酸的方法。
Chemistry. 2000 Jul 3;6(13):2435-48. doi: 10.1002/1521-3765(20000703)6:13<2435::aid-chem2435>3.0.co;2-z.
4
Asymmetric Synthesis of Hispidanin A and Related Diterpenoids.（标题）：他皮他宁 A 及其相关二萜的不对称合成。
Chemistry. 2018 Jun 26;24(36):9120-9129. doi: 10.1002/chem.201801156. Epub 2018 Jun 6.
5
DFT study of the mechanism and stereochemistry of the Rh(I)-catalyzed Diels-Alder reactions between electronically neutral dienes and dienophiles.铑（I）催化的电中性双烯和亲双烯体之间的狄尔斯-阿尔德反应的机理和立体化学的密度泛函理论研究
J Org Chem. 2014 Dec 19;79(24):11949-60. doi: 10.1021/jo5017844. Epub 2014 Oct 16.
6
Enantioselective biomimetic total syntheses of kuwanons I and J and brosimones A and B.对库烷酮 I 和 J 以及布罗西诺内 A 和 B 的对映选择性仿生全合成。
Angew Chem Int Ed Engl. 2014 Aug 25;53(35):9257-61. doi: 10.1002/anie.201404499. Epub 2014 Jul 7.
7
endo/exo stereoselectivity in Diels-Alder reactions of α,β-dialkylated conjugated enals to cyclic 1,3-dienes: intermediates in the synthesis of (-)-β-santalol and its analogs.α,β-二烷基共轭烯醛与环状1,3-二烯发生狄尔斯-阿尔德反应中的内/外型立体选择性：（-）-β-檀香醇及其类似物合成中的中间体
Chem Biodivers. 2014 Oct;11(10):1470-516. doi: 10.1002/cbdv.201400060.
8
Biomimetic Total Synthesis of (±)-Griffipavixanthone via a Cationic Cycloaddition-Cyclization Cascade.仿生全合成（±）- Griffipavixanthone 通过阳离子环加成-环化级联反应。
J Am Chem Soc. 2017 Oct 11;139(40):14053-14056. doi: 10.1021/jacs.7b09265. Epub 2017 Oct 2.
9
Enantioselective and Collective Total Syntheses of Xanthanolides.手性选择性和集体全合成的 xanthanolides。
Angew Chem Int Ed Engl. 2017 Dec 18;56(51):16323-16327. doi: 10.1002/anie.201710846. Epub 2017 Nov 27.
10
Application of the aza-Diels-Alder reaction in the synthesis of natural products.氮杂狄尔斯-阿尔德反应在天然产物合成中的应用。
Org Biomol Chem. 2017 Apr 11;15(15):3105-3129. doi: 10.1039/c6ob02761j.

本文引用的文献

1
InI-catalyzed polyene cyclization of allenes and its application in the total synthesis of seven abietane-type diterpenoids.铟催化的丙二烯多烯环化反应及其在七种松香烷型二萜全合成中的应用。
Chem Sci. 2022 Nov 2;13(46):13893-13897. doi: 10.1039/d2sc04229k. eCollection 2022 Nov 30.
2
Total syntheses of naturally occurring antiviral indolosesquiterpene alkaloids, xiamycins C-F Csp-H functionalization.天然存在的抗病毒吲哚倍半萜生物碱夏霉素C - F的全合成：Csp - H官能团化
Chem Sci. 2022 Sep 21;13(39):11666-11671. doi: 10.1039/d2sc03479d. eCollection 2022 Oct 12.
3
Catalytic Asymmetric Inverse-Electron-Demand Diels-Alder Reactions of 2-Pyrones with Indenes: Total Syntheses of Cephanolides A and B.
2-吡喃酮与茚的催化不对称逆电子需求 Diels-Alder 反应： Cephanolides A 和 B 的全合成。
Angew Chem Int Ed Engl. 2021 Dec 13;60(51):26610-26615. doi: 10.1002/anie.202112223. Epub 2021 Nov 9.
4
Origin of rate enhancement and asynchronicity in iminium catalyzed Diels-Alder reactions.亚胺催化的狄尔斯-阿尔德反应中速率增强和异步性的起源
Chem Sci. 2020 Jul 9;11(31):8105-8112. doi: 10.1039/d0sc02901g.
5
Total Synthesis of the Norditerpenoids (±)-Cephanolides A-D.总合成 Norditerpenoids(±)-Cephanolides A-D。
J Am Chem Soc. 2021 Feb 24;143(7):2710-2715. doi: 10.1021/jacs.1c00293. Epub 2021 Feb 12.
6
Cobalt-Catalyzed Hydrogen-Atom Transfer Induces Bicyclizations that Tolerate Electron-Rich and Electron-Deficient Intermediate Alkenes.钴催化的氢原子转移诱导可耐受富电子和缺电子中间烯烃的双环化反应。
Angew Chem Int Ed Engl. 2020 Apr 6;59(15):6115-6121. doi: 10.1002/anie.202000252. Epub 2020 Feb 25.
7
Total Syntheses of Aromatic Abietane Diterpenoids Utilizing Advances in the Pummerer Rearrangement.利用 Pummerer 重排反应的进展实现芳香枞烷二萜的全合成。
Org Lett. 2018 Sep 21;20(18):5546-5549. doi: 10.1021/acs.orglett.8b02060. Epub 2018 Sep 10.
8
Gold(I)-Catalyzed Intramolecular Diels-Alder Reaction: Evolution of Trappable Intermediates via Asynchronous Transition States.金（I）催化的分子内狄尔斯-阿尔德反应：通过异步过渡态形成可捕获中间体的过程
J Org Chem. 2018 Sep 21;83(18):11167-11177. doi: 10.1021/acs.joc.8b01752. Epub 2018 Aug 3.
9
Total Synthesis of Septedine and 7-Deoxyseptedine.Septedine和7-脱氧Septedine的全合成。
J Am Chem Soc. 2018 Jul 25;140(29):9025-9029. doi: 10.1021/jacs.8b03712. Epub 2018 Jul 11.
10
Modified Abietane Diterpenoids from Whole Plants of Selaginella moellendorffii.卷柏全草中的改性枞型二萜。
J Nat Prod. 2018 Feb 23;81(2):418-422. doi: 10.1021/acs.jnatprod.7b00909. Epub 2018 Feb 7.