利松烷酸 A 的全合成。
Total Synthesis of Lissodendoric Acid A.
机构信息
Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA 90095, USA.
Department of Chemistry, Hamline University, St. Paul, Minnesota, 55104, USA.
出版信息
Angew Chem Int Ed Engl. 2024 Aug 5;63(32):e202406676. doi: 10.1002/anie.202406676. Epub 2024 Jul 3.
Abstract
We describe a full account of our synthetic strategy leading to the first total synthesis of the manzamine alkaloid lissodendoric acid A . These efforts demonstrate that strained cyclic allenes are valuable synthetic building blocks and can be employed efficiently in total synthesis.
摘要
我们描述了导致曼扎明生物碱利松多里酸 A 的首次全合成的综合策略的完整说明。这些努力表明，应变环状丙二烯是有价值的合成砌块，并可在全合成中有效地应用。
相似文献
1
Total Synthesis of Lissodendoric Acid A.利松烷酸 A 的全合成。
Angew Chem Int Ed Engl. 2024 Aug 5;63(32):e202406676. doi: 10.1002/anie.202406676. Epub 2024 Jul 3.
2
Total synthesis of lissodendoric acid A via stereospecific trapping of a strained cyclic allene.通过立体选择性捕获应变环状丙二烯，全合成 lissodendoric 酸 A。
Science. 2023 Jan 20;379(6629):261-265. doi: 10.1126/science.ade0032. Epub 2023 Jan 19.
3
Total Synthesis of Chartelline C.Chartelline C的全合成。
J Am Chem Soc. 2025 Jul 16;147(28):24921-24931. doi: 10.1021/jacs.5c07148. Epub 2025 Jul 1.
4
Reactivity of Anomalous Aziridines for Versatile Access to High Fsp Amine Chemical Space.异常氮丙啶对广泛进入高Fsp胺化学空间的反应活性。
Acc Chem Res. 2025 Jan 21;58(2):231-249. doi: 10.1021/acs.accounts.4c00670. Epub 2024 Dec 30.
5
Selective Oxidation of Disparate Functional Groups Mediated by a Common Aspartic Acid-Based Peptide Catalyst Platform.由基于天冬氨酸的常见肽催化剂平台介导的不同官能团的选择性氧化
Acc Chem Res. 2025 Jun 18. doi: 10.1021/acs.accounts.5c00247.
6
The Lived Experience of Autistic Adults in Employment: A Systematic Search and Synthesis.成年自闭症患者的就业生活经历：系统检索与综述
Autism Adulthood. 2024 Dec 2;6(4):495-509. doi: 10.1089/aut.2022.0114. eCollection 2024 Dec.
7
Organic Synthesis Away from Equilibrium: Contrathermodynamic Transformations Enabled by Excited-State Electron Transfer.远离平衡态的有机合成：由激发态电子转移实现的反热力学转变
Acc Chem Res. 2024 Jul 2;57(13):1827-1838. doi: 10.1021/acs.accounts.4c00227. Epub 2024 Jun 21.
8
Nucleic Acid Nanocapsules as a New Platform to Deliver Therapeutic Nucleic Acids for Gene Regulation.核酸纳米胶囊作为用于基因调控的治疗性核酸递送新平台。
Acc Chem Res. 2025 Jul 1;58(13):1951-1962. doi: 10.1021/acs.accounts.5c00126. Epub 2025 Jun 9.
9
Total Synthesis and Structural Revision of (±)-Mauritamide B.（±）-毛里塔酰胺B的全合成及结构修正
J Nat Prod. 2025 Mar 28;88(3):806-814. doi: 10.1021/acs.jnatprod.5c00019. Epub 2025 Feb 21.
10
Gender differences in the context of interventions for improving health literacy in migrants: a qualitative evidence synthesis.移民健康素养提升干预措施背景下的性别差异：一项定性证据综合分析
Cochrane Database Syst Rev. 2024 Dec 12;12(12):CD013302. doi: 10.1002/14651858.CD013302.pub2.
引用本文的文献
1
Development of a Vinylated Cyclic Allene: A Fleeting Strained Diene for the Diels-Alder Reaction.乙烯基化环丙二烯的开发：一种用于狄尔斯-阿尔德反应的瞬态张力二烯。
Angew Chem Int Ed Engl. 2025 Aug 11;64(33):e202510319. doi: 10.1002/anie.202510319. Epub 2025 Jun 26.
2
Diels-Alder Cycloadditions of Oxacyclic Allenes and α-Pyrones.氧杂环丙二烯与α-吡喃酮的狄尔斯-阿尔德环加成反应。
Org Lett. 2024 Aug 2;26(30):6465-6470. doi: 10.1021/acs.orglett.4c02294. Epub 2024 Jul 24.
本文引用的文献
1
Cyclic Allene Approach to the Manzamine Alkaloid Keramaphidin B.环状丙二烯方法合成曼扎明生物碱凯拉马芬丁 B。
Org Lett. 2023 Aug 4;25(30):5553-5557. doi: 10.1021/acs.orglett.3c01489. Epub 2023 Jun 30.
2
Stereoselective Intramolecular [2+2] Trapping of 1,2-Cyclohexadienes: a Route to Rigid, Angularly Fused Tricyclic Scaffolds.1,2-环己二烯的立体选择性分子内[2+2]捕获：通向刚性、角稠合三环骨架的途径。
Chemistry. 2023 Sep 12;29(51):e202301668. doi: 10.1002/chem.202301668. Epub 2023 Aug 7.
3
A Distinct Mode of Strain-Driven Cyclic Allene Reactivity: Group Migration to the Central Allene Carbon Atom.应变驱动的环丙炔反应的独特模式：基团迁移到中央丙炔碳原子。
J Am Chem Soc. 2023 May 3;145(17):9867-9875. doi: 10.1021/jacs.3c02469. Epub 2023 Apr 22.
4
Total synthesis of lissodendoric acid A via stereospecific trapping of a strained cyclic allene.通过立体选择性捕获应变环状丙二烯，全合成 lissodendoric 酸 A。
Science. 2023 Jan 20;379(6629):261-265. doi: 10.1126/science.ade0032. Epub 2023 Jan 19.
5
Revisiting the manzamine biosynthetic hypothesis.重新审视马钱宁生物合成假说。
Nat Prod Rep. 2023 May 24;40(5):964-971. doi: 10.1039/d2np00082b.
6
Assessment on facile Diels-Alder approach of α-pyrone and terpenoquinone for the expedient synthesis of various natural scaffolds.关于α-吡喃酮与萜烯醌通过简便的狄尔斯-阿尔德反应途径快速合成各种天然骨架的评估。
Nat Prod Bioprospect. 2022 Mar 31;12(1):12. doi: 10.1007/s13659-022-00333-4.
7
Leveraging Fleeting Strained Intermediates to Access Complex Scaffolds.利用瞬态应变中间体构建复杂骨架。
JACS Au. 2021 Jul 26;1(7):897-912. doi: 10.1021/jacsau.1c00214. Epub 2021 Jun 23.
8
Origins of Endo Selectivity in Diels-Alder Reactions of Cyclic Allene Dienophiles.环状丙二烯亲二烯体的 Diels-Alder 反应中endo 选择性的起源。
Angew Chem Int Ed Engl. 2021 Jun 25;60(27):14989-14997. doi: 10.1002/anie.202101809. Epub 2021 May 28.
9
-Silylaryl Triflates: A Journey of Kobayashi Aryne Precursors.硅芳基三氟甲磺酸酯：小林芳炔前体的探索之旅。
Chem Rev. 2021 Apr 14;121(7):3892-4044. doi: 10.1021/acs.chemrev.0c01011. Epub 2021 Feb 18.
10
Generation and trapping of electron-deficient 1,2-cyclohexadienes. Unexpected hetero-Diels-Alder reactivity.生成和捕获缺电子 1,2-环己二烯。出乎意料的杂 Diels-Alder 反应性。
Org Biomol Chem. 2021 Jan 21;19(2):399-405. doi: 10.1039/d0ob02285c.
Zotero 插件