• 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

以对映体富集形式合成氯代硫脂类化合物达尼卡利平A、贻贝脂素A和马尔哈门脂素A的通用方法。

General approach to the synthesis of the chlorosulfolipids danicalipin A, mytilipin A, and malhamensilipin A in enantioenriched form.

作者信息

Chung Won-jin, Carlson Joseph S, Vanderwal Christopher D

机构信息

Department of Chemistry, 1102 Natural Sciences II, University of California , Irvine, California 92697-2025, United States.

出版信息

J Org Chem. 2014 Mar 7;79(5):2226-41. doi: 10.1021/jo5000829. Epub 2014 Feb 13.

DOI:10.1021/jo5000829
PMID:24494597
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3954434/
Abstract

A second-generation synthesis of three structurally related chlorosulfolipids has been developed. Key advances include highly stereocontrolled additions to α,β-dichloroaldehydes, kinetic resolutions of complex chlorinated vinyl epoxide intermediates, and Z-selective alkene cross metatheses of cis-vinyl epoxides. This strategy facilitated the synthesis of enantioenriched danicalipin A, mytilipin A, and malhamensilipin A in nine, eight, and 11 steps, respectively.

摘要

已开发出三种结构相关的氯代硫脂的第二代合成方法。关键进展包括对α,β-二氯醛的高度立体控制加成、复杂氯化环氧乙烯中间体的动力学拆分以及顺式环氧乙烯的Z选择性烯烃交叉复分解反应。该策略分别以九步、八步和十一步促进了对映体富集的达尼卡利平A、贻贝脂素A和马尔哈门西脂素A的合成。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fbcc/3954434/48cd98494272/jo-2014-000829_0020.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fbcc/3954434/3cfcc1482746/jo-2014-000829_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fbcc/3954434/970b0892883f/jo-2014-000829_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fbcc/3954434/529b83d12f36/jo-2014-000829_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fbcc/3954434/891a04805894/jo-2014-000829_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fbcc/3954434/cfac71a9e2a2/jo-2014-000829_0010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fbcc/3954434/72e8170ca02c/jo-2014-000829_0011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fbcc/3954434/e8aada17baf9/jo-2014-000829_0012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fbcc/3954434/4cae601f6381/jo-2014-000829_0013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fbcc/3954434/0886ecb59a92/jo-2014-000829_0014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fbcc/3954434/43e3ee0683f6/jo-2014-000829_0015.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fbcc/3954434/61486c5df0b1/jo-2014-000829_0016.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fbcc/3954434/eefbf5a9c6b7/jo-2014-000829_0017.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fbcc/3954434/f9d5d75345ef/jo-2014-000829_0018.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fbcc/3954434/76502857669e/jo-2014-000829_0019.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fbcc/3954434/48cd98494272/jo-2014-000829_0020.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fbcc/3954434/3cfcc1482746/jo-2014-000829_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fbcc/3954434/970b0892883f/jo-2014-000829_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fbcc/3954434/529b83d12f36/jo-2014-000829_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fbcc/3954434/891a04805894/jo-2014-000829_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fbcc/3954434/cfac71a9e2a2/jo-2014-000829_0010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fbcc/3954434/72e8170ca02c/jo-2014-000829_0011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fbcc/3954434/e8aada17baf9/jo-2014-000829_0012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fbcc/3954434/4cae601f6381/jo-2014-000829_0013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fbcc/3954434/0886ecb59a92/jo-2014-000829_0014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fbcc/3954434/43e3ee0683f6/jo-2014-000829_0015.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fbcc/3954434/61486c5df0b1/jo-2014-000829_0016.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fbcc/3954434/eefbf5a9c6b7/jo-2014-000829_0017.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fbcc/3954434/f9d5d75345ef/jo-2014-000829_0018.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fbcc/3954434/76502857669e/jo-2014-000829_0019.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/fbcc/3954434/48cd98494272/jo-2014-000829_0020.jpg

相似文献

1
General approach to the synthesis of the chlorosulfolipids danicalipin A, mytilipin A, and malhamensilipin A in enantioenriched form.以对映体富集形式合成氯代硫脂类化合物达尼卡利平A、贻贝脂素A和马尔哈门脂素A的通用方法。
J Org Chem. 2014 Mar 7;79(5):2226-41. doi: 10.1021/jo5000829. Epub 2014 Feb 13.
2
Approaches to the chemical synthesis of the chlorosulfolipids.氯磺酸酯的化学合成方法。
Acc Chem Res. 2014 Feb 18;47(2):718-28. doi: 10.1021/ar400246w. Epub 2014 Jan 8.
3
A synthesis of the chlorosulfolipid mytilipin A via a longest linear sequence of seven steps.经最长线性序列的七步反应合成氯化磺脂 mytilipin A。
Angew Chem Int Ed Engl. 2013 Sep 16;52(38):10052-5. doi: 10.1002/anie.201304565. Epub 2013 Aug 8.
4
Stereochemical Revision, Total Synthesis, and Solution State Conformation of the Complex Chlorosulfolipid Mytilipin B.立体化学修订、全合成及复杂氯代磺脂类肌肽 B 的溶液构象。
J Am Chem Soc. 2019 Jul 3;141(26):10510-10519. doi: 10.1021/jacs.9b05013. Epub 2019 Jun 19.
5
Asymmetric total synthesis of (+)-danicalipin A.(+)-丹卡脂素 A 的不对称全合成。
Org Lett. 2011 Mar 4;13(5):908-11. doi: 10.1021/ol1029518. Epub 2011 Feb 2.
6
Relative stereochemistry determination and synthesis of the major chlorosulfolipid from Ochromonas danica.嗜铬绿藻中主要氯代硫脂的相对立体化学测定与合成
J Am Chem Soc. 2009 Jun 10;131(22):7570-2. doi: 10.1021/ja902138w.
7
Asymmetric total synthesis of danicalipin A and evaluation of biological activity.丹卡林 A 的不对称全合成及生物活性评价。
Org Lett. 2011 Mar 4;13(5):904-7. doi: 10.1021/ol102882a. Epub 2011 Feb 3.
8
Multicomponent linchpin couplings. Reaction of dithiane anions with terminal epoxides, epichlorohydrin, and vinyl epoxides: efficient, rapid, and stereocontrolled assembly of advanced fragments for complex molecule synthesis.多组分关键偶联反应。二硫烷阴离子与末端环氧化物、环氧氯丙烷和乙烯基环氧化物的反应：用于复杂分子合成的高级片段的高效、快速且立体控制的组装。
J Am Chem Soc. 2003 Nov 26;125(47):14435-45. doi: 10.1021/ja0376238.
9
Synthesis and characterization of all four diastereomers of 3,4-dichloro-2-pentanol, motifs relevant to the chlorosulfolipids.合成并表征 3,4-二氯-2-戊醇的全部四个非对映异构体，这些异构体与氯磺酸脂有关。
J Org Chem. 2009 Mar 6;74(5):2175-8. doi: 10.1021/jo802390e.
10
Biological Investigations of (+)-Danicalipin A Enabled Through Synthesis.通过合成对 (+)-丹卡脂素 A 进行的生物学研究。
Angew Chem Int Ed Engl. 2016 Jan 11;55(2):639-43. doi: 10.1002/anie.201509082. Epub 2015 Nov 27.

引用本文的文献

1
Stereospecific syn-dihalogenations and regiodivergent syn-interhalogenation of alkenes via vicinal double electrophilic activation strategy.通过邻位双亲电活化策略实现烯烃的立体选择性顺式二卤代反应和区域发散性顺式卤间代反应。
Nat Commun. 2024 May 2;15(1):3710. doi: 10.1038/s41467-024-47942-w.
2
Naturally Occurring Organohalogen Compounds-A Comprehensive Review.天然有机卤代化合物综述。
Prog Chem Org Nat Prod. 2023;121:1-546. doi: 10.1007/978-3-031-26629-4_1.
3
Total Synthesis of the Dihydrooxepine-Spiroisoxazoline Natural Product Psammaplysin A.

本文引用的文献

1
Ruthenium-catalysed -selective cross metathesis of allylic-substituted olefins.钌催化的烯丙基取代烯烃的 - 选择性交叉复分解反应。
Chem Sci. 2014 Feb;5(2):501-506. doi: 10.1039/C3SC52806E.
2
Approaches to the chemical synthesis of the chlorosulfolipids.氯磺酸酯的化学合成方法。
Acc Chem Res. 2014 Feb 18;47(2):718-28. doi: 10.1021/ar400246w. Epub 2014 Jan 8.
3
Investigations into Ruthenium Metathesis Catalysts with Six-Membered Chelating NHC Ligands: Relationship between Catalyst Structure and Stereoselectivity.含六元螯合NHC配体的钌复分解催化剂的研究：催化剂结构与立体选择性之间的关系
二氢恶嗪-螺噁唑啉天然产物 Psammaplysin A 的全合成。
J Am Chem Soc. 2022 Nov 2;144(43):19704-19708. doi: 10.1021/jacs.2c10010. Epub 2022 Oct 21.
4
The Recurring Roles of Chlorine in Synthetic and Biological Studies of the Lissoclimides.氯在 Lissoclimides 的合成和生物研究中的反复作用。
Acc Chem Res. 2021 Mar 2;54(5):1131-1142. doi: 10.1021/acs.accounts.0c00866. Epub 2021 Feb 5.
5
Catalytic Enantioselective Dihalogenation in Total Synthesis.催化对映选择性双卤化反应在全合成中的应用。
Acc Chem Res. 2018 May 15;51(5):1260-1271. doi: 10.1021/acs.accounts.8b00064. Epub 2018 Apr 17.
6
Stereochemistry and biological activity of chlorinated lipids: a study of danicalipin A and selected diastereomers.氯化脂质的立体化学与生物活性：对达尼卡利平A及选定非对映异构体的研究
Chem Sci. 2017 Oct 1;8(10):6904-6910. doi: 10.1039/c7sc03124f. Epub 2017 Aug 9.
7
Synthesis of malhamensilipin A exploiting iterative epoxidation/chlorination: experimental and computational analysis of epoxide-derived chloronium ions.利用迭代环氧化/氯化反应合成马尔哈门西利平A：环氧化物衍生的氯鎓离子的实验与计算分析
Chem Sci. 2016 Dec 11;7(12):7040-7049. doi: 10.1039/c6sc03012b. Epub 2016 Aug 2.
8
Mn-, Fe-, and Co-Catalyzed Radical Hydrofunctionalizations of Olefins.锰、铁和钴催化的烯烃自由基氢官能化反应
Chem Rev. 2016 Aug 10;116(15):8912-9000. doi: 10.1021/acs.chemrev.6b00334. Epub 2016 Jul 27.
9
Catalytic Enantioselective Dihalogenation and the Selective Synthesis of (-)-Deschloromytilipin A and (-)-Danicalipin A.催化对映选择性二卤化反应及（-）-去氯米蒂利平A和（-）-达尼卡利平A的选择性合成
J Am Chem Soc. 2016 Apr 20;138(15):5150-8. doi: 10.1021/jacs.6b01643. Epub 2016 Apr 8.
10
The Alga Ochromonas danica Produces Bromosulfolipids.藻类硅藻产生溴代磺基脂类。
Org Lett. 2016 Mar 4;18(5):1124-7. doi: 10.1021/acs.orglett.6b00230. Epub 2016 Feb 18.
Organometallics. 2013 Sep 23;32(18). doi: 10.1021/om4006966.
4
Catalytic enantioselective dibromination of allylic alcohols.催化对映选择性烯丙醇的双溴化反应。
J Am Chem Soc. 2013 Sep 4;135(35):12960-3. doi: 10.1021/ja4083182. Epub 2013 Aug 21.
5
A synthesis of the chlorosulfolipid mytilipin A via a longest linear sequence of seven steps.经最长线性序列的七步反应合成氯化磺脂 mytilipin A。
Angew Chem Int Ed Engl. 2013 Sep 16;52(38):10052-5. doi: 10.1002/anie.201304565. Epub 2013 Aug 8.
6
Alkene chemoselectivity in ruthenium-catalyzed Z-selective olefin metathesis.钌催化 Z-选择性烯烃复分解反应中的烯烃化学选择性。
Angew Chem Int Ed Engl. 2013 Aug 19;52(34):9001-4. doi: 10.1002/anie.201302724. Epub 2013 Jul 5.
7
Highly Z-selective and enantioselective ring-opening/cross-metathesis catalyzed by a resolved stereogenic-at-Ru complex.高 Z-选择性和对映选择性的开环/交叉复分解反应，由手性钌配合物催化。
J Am Chem Soc. 2013 Jul 17;135(28):10183-5. doi: 10.1021/ja4046422. Epub 2013 Jul 3.
8
Synthesis of highly cis, syndiotactic polymers via ring-opening metathesis polymerization using ruthenium metathesis catalysts.通过使用钌复分解催化剂进行开环复分解聚合来合成高顺式、间同立构聚合物。
J Am Chem Soc. 2013 Jul 10;135(27):10032-5. doi: 10.1021/ja405559y. Epub 2013 Jun 25.
9
A practical method for the synthesis of highly enantioenriched trans-1,2-amino alcohols.一种高效合成高对映选择性反式-1,2-氨基醇的实用方法。
Org Lett. 2013 Jun 21;15(12):2895-7. doi: 10.1021/ol401013s. Epub 2013 Jun 6.
10
Deracemization of amino acids by partial sublimation and via homochiral self-organization.通过部分升华和同手性自组装拆分氨基酸外消旋体。
Orig Life Evol Biosph. 2013 Apr;43(2):129-35. doi: 10.1007/s11084-013-9333-6. Epub 2013 May 21.