通过TiCl(4)促进的氮杂-[3 + 3]环化反应，以立体发散的方法构建莱帕定家族中C2,8a-顺式和C2,8a-反式相对立体化学结构的方法。
A Stereodivergent Approach for Accessing Both C2,8a-Syn and C2,8a-Anti Relative Stereochemical Manifolds in the Lepadin Family via a TiCL(4)-Promoted Aza-[3 + 3] Annulation.
作者信息
Li Gang, Carlson Lauren J, Sagamanova Irina K, Slafer Brian W, Hsung Richard P, Gilardi Claudio, Sklenicka Heather M, Sydroenko Nadiya
机构信息
Division of Pharmaceutical Sciences and Department of Chemistry, Wisconsin Center for Natural Products Research, School of Pharmacy, Rennebohm Hall, University of Wisconsin, Madison, WI 53705.
出版信息
Synthesis (Stuttg). 2009 Sep 1;2009(17):2905. doi: 10.1055/s-0029-1216920.
Abstract
Details in developing a stereodivergent approach to the lepadin family and establishing an entry to both C2,8a-syn and C2,8a-anti relative stereochemical manifolds through a common intermediate are described here. This works paves a foundation for constructing all members of the lepadin family, which consists of three subsets based on an array of interesting relative configurations. These efforts underline the prominence of aza-[3 + 3] annulation as a unified strategy in alkaloid synthesis.
摘要
本文描述了开发一种立体发散方法来合成勒帕定家族化合物，并通过一个共同中间体构建C2,8a-顺式和C2,8a-反式相对立体化学异构体库的详细过程。这项工作为构建勒帕定家族的所有成员奠定了基础，该家族基于一系列有趣的相对构型可分为三个子集。这些努力突出了氮杂-[3 + 3]环化反应作为生物碱合成中一种统一策略的重要性。
相似文献
1
A Stereodivergent Approach for Accessing Both C2,8a-Syn and C2,8a-Anti Relative Stereochemical Manifolds in the Lepadin Family via a TiCL(4)-Promoted Aza-[3 + 3] Annulation.通过TiCl(4)促进的氮杂-[3 + 3]环化反应，以立体发散的方法构建莱帕定家族中C2,8a-顺式和C2,8a-反式相对立体化学结构的方法。
Synthesis (Stuttg). 2009 Sep 1;2009(17):2905. doi: 10.1055/s-0029-1216920.
2
Total synthesis of (+)-lepadin F.(+)-勒帕定F的全合成
Org Lett. 2008 Nov 6;10(21):4991-4. doi: 10.1021/ol802068q. Epub 2008 Sep 27.
3
Establishing the concept of aza-[3 + 3] annulations using enones as a key expansion of this unified strategy in alkaloid synthesis.利用烯酮作为这一统一策略在生物碱合成中的关键扩展，建立氮杂-[3 + 3]环加成的概念。
Beilstein J Org Chem. 2013 Jun 18;9:1170-8. doi: 10.3762/bjoc.9.131. Print 2013.
4
Synergistic Catalysis Involving Palladium for Stereodivergent Csp3-Csp3 Coupling Reactions.涉及钯的协同催化用于立体发散性Csp3-Csp3偶联反应
Acc Chem Res. 2024 Jan 31. doi: 10.1021/acs.accounts.3c00639.
5
Assignment of the C5' relative stereochemistry in (+)-lepadin F and (+)-lepadin G and absolute configuration of (+)-lepadin G.（+）-勒帕定F中C5′相对立体化学的确定以及（+）-勒帕定G的绝对构型
Org Lett. 2009 Oct 15;11(20):4616-9. doi: 10.1021/ol9018997.
6
An intramolecular aza-[3+3] annulation approach to azaphenalene alkaloids. Total synthesis of myrrhine.一种用于氮杂菲生物碱的分子内氮杂-[3+3]环化方法。没药碱的全合成。
J Org Chem. 2007 Mar 30;72(7):2476-84. doi: 10.1021/jo062533h. Epub 2007 Mar 6.
7
A General Approach to the Quinolizidine Alkaloids via an Intramolecular Aza-[3 + 3] Annulation. Synthesis of (±)-2-Deoxy-Lasubine II.一种通过分子内氮杂-[3 + 3]环化反应合成喹诺里西啶生物碱的通用方法。（±）-2-脱氧拉苏宾II的合成。
Synlett. 2008 Jan 1;2009(2):237-240. doi: 10.1055/s-0028-1087661.
8
Stereodivergent Construction of 3,3'-Disubstituted Oxindoles via One-Pot Sequential Allylation/Alkylation and Its Application to the Total Synthesis of Trigolute B and D.通过一锅法连续烯丙基化/烷基化立体发散构建3,3'-二取代氧化吲哚及其在Trigolute B和D全合成中的应用
J Am Chem Soc. 2025 Mar 5;147(9):7729-7740. doi: 10.1021/jacs.4c17425. Epub 2025 Jan 27.
9
Insights into Cytotoxic Behavior of Lepadins and Structure Elucidation of the New Alkaloid Lepadin L from the Mediterranean Ascidian .从地中海贻贝中了解 Lepadin 的细胞毒性行为及新生物碱 Lepadin L 的结构解析。
Mar Drugs. 2022 Jan 11;20(1):65. doi: 10.3390/md20010065.
10
Direct, Stereodivergent, and Catalytic Michael Additions of Thioimides to α,β-Unsaturated Aldehydes - Total Synthesis of Tapentadol.硫代酰亚胺与α,β-不饱和醛的直接、立体发散性和催化迈克尔加成反应——他喷他多的全合成
Angew Chem Int Ed Engl. 2024 Mar 18;63(12):e202319308. doi: 10.1002/anie.202319308. Epub 2024 Feb 15.
引用本文的文献
1
Domino Aldol-SAr-Dehydration Sequence for [3+3] Annulations to Prepare Quinolin-2(1)-ones and 1,8-Naphthyridin-2(1)-ones.用于[3+3]环化反应制备喹啉-2(1)-酮和1,8-萘啶-2(1)-酮的多米诺醛醇缩合-SAr-脱水序列
Molecules. 2023 Aug 3;28(15):5856. doi: 10.3390/molecules28155856.
2
Asymmetric aza-[3+3] annulation in the synthesis of indolizidines: an unexpected reversal of regiochemistry.不对称氮杂-[3+3]环化反应在吲哚里嗪类化合物的合成中的应用：区域化学的意外反转。
Org Lett. 2011 Aug 19;13(16):4402-5. doi: 10.1021/ol2017438. Epub 2011 Jul 25.
3
Aza-[3 + 3] Annulations: A New Unified Strategy in Alkaloid Synthesis.氮杂-[3 + 3]环合反应：生物碱合成中的一种新的统一策略。
Curr Org Synth. 2010 Aug 1;7(4):363-401. doi: 10.2174/157017910791414490.
本文引用的文献
1
A General Approach to the Quinolizidine Alkaloids via an Intramolecular Aza-[3 + 3] Annulation. Synthesis of (±)-2-Deoxy-Lasubine II.一种通过分子内氮杂-[3 + 3]环化反应合成喹诺里西啶生物碱的通用方法。（±）-2-脱氧拉苏宾II的合成。
Synlett. 2008 Jan 1;2009(2):237-240. doi: 10.1055/s-0028-1087661.
2
Phosphine-promoted [3 + 3] annulations of aziridines with allenoates: facile entry into highly functionalized tetrahydropyridines.磷化氢促进氮丙啶与联烯酸酯的[3 + 3]环化反应：便捷合成高度官能化的四氢吡啶
J Am Chem Soc. 2009 May 13;131(18):6318-9. doi: 10.1021/ja8097349.
3
Aza- and Carbo-[3 + 3] Annulations of Exo-Cyclic Vinylogous Amides and Urethanes. Synthesis of Tetrahydroindolizidines and An Unexpected Formation of Hexahydroquinolines.外环烯丙型酰胺和氨基甲酸酯的氮杂-和碳杂-[3 + 3]环合反应。四氢吲哚嗪的合成及六氢喹啉的意外生成。
Tetrahedron. 2008 Jan 28;64(5):883-893. doi: 10.1016/j.tet.2007.09.089.
4
Vilsmeier reaction of enaminones: efficient synthesis of halogenated pyridin-2(1H)-ones.烯胺酮的 Vilsmeier 反应：高效合成卤代吡啶-2(1H)-酮。
J Org Chem. 2008 Dec 5;73(23):9504-7. doi: 10.1021/jo801959j.
5
Total synthesis of (+)-lepadin F.(+)-勒帕定F的全合成
Org Lett. 2008 Nov 6;10(21):4991-4. doi: 10.1021/ol802068q. Epub 2008 Sep 27.
6
Diphenylprolinol silyl ether as a catalyst in an enantioselective, catalytic, formal aza [3+3] cycloaddition reaction for the formation of enantioenriched piperidines.二苯基脯氨醇硅醚作为一种催化剂，用于对映选择性催化形式氮杂[3+3]环加成反应，以形成对映体富集的哌啶。
Angew Chem Int Ed Engl. 2008;47(21):4012-5. doi: 10.1002/anie.200800662.
7
Total Synthesis of ent-lepadin F and G by a tandem ene-yne-ene ring closing metathesis.通过串联烯-炔-烯闭环复分解反应全合成对映-勒帕定F和G。
J Org Chem. 2008 Apr 18;73(8):3088-93. doi: 10.1021/jo7027079. Epub 2008 Mar 22.
8
Asymmetric annulation toward pyrrolopiperazinones: concise enantioselective syntheses of pyrrole alkaloid natural products.吡咯并哌嗪酮的不对称环化反应：吡咯生物碱天然产物的简洁对映选择性合成
Org Lett. 2007 Jun 7;9(12):2357-9. doi: 10.1021/ol070742y. Epub 2007 May 12.
9
Thirty-five years of synthetic studies directed towards the histrionicotoxin family of alkaloids.针对生物碱类组氨酰毒碱家族的35年合成研究。
Nat Prod Rep. 2007 Apr;24(2):298-326. doi: 10.1039/b604203c. Epub 2007 Feb 21.
10
An intramolecular aza-[3+3] annulation approach to azaphenalene alkaloids. Total synthesis of myrrhine.一种用于氮杂菲生物碱的分子内氮杂-[3+3]环化方法。没药碱的全合成。
J Org Chem. 2007 Mar 30;72(7):2476-84. doi: 10.1021/jo062533h. Epub 2007 Mar 6.
Zotero 插件