ent-[3]-Ladderanol 的合成：烯丙基酮和烯烃的分子内手性转移 [2+2] 环加成反应的开发与应用。
Synthesis of ent-[3]-Ladderanol: Development and Application of Intramolecular Chirality Transfer [2+2] Cycloadditions of Allenic Ketones and Alkenes.
机构信息
Department of Chemistry, Indiana University , 800 E. Kirkwood Avenue, Bloomington, Indiana 47405, United States.
出版信息
J Am Chem Soc. 2017 Oct 18;139(41):14392-14395. doi: 10.1021/jacs.7b09844. Epub 2017 Oct 6.
Abstract
An enantioselective synthesis of ent-[3]-ladderanol is presented. The ladderanes are an interesting class of molecules for their unique structure of fused cyclobutane rings as well as their perceived biological function of organism protection. The route hinges on the development and application of a chirality transfer [2+2] cycloaddition of an allenic ketone and alkene. Further stereocontrolled transformations allowed for completion of the synthesis. The scope of the chirality transfer [2+2] cycloaddition is also presented.
摘要
本文介绍了（3）-升海松烷的对映选择性合成。 ladderanes 因其独特的稠合环丁烷结构以及被认为具有生物保护功能而成为一类有趣的分子。该路线的关键在于发展和应用烯丙基酮和烯烃的手性转移 [2+2]环加成反应。进一步的立体控制转化完成了合成。还介绍了手性转移 [2+2]环加成的范围。
相似文献
1
Synthesis of ent-[3]-Ladderanol: Development and Application of Intramolecular Chirality Transfer [2+2] Cycloadditions of Allenic Ketones and Alkenes.ent-[3]-Ladderanol 的合成：烯丙基酮和烯烃的分子内手性转移 [2+2] 环加成反应的开发与应用。
J Am Chem Soc. 2017 Oct 18;139(41):14392-14395. doi: 10.1021/jacs.7b09844. Epub 2017 Oct 6.
2
Synthesis of (-)-Hebelophyllene E: An Entry to Geminal Dimethyl-Cyclobutanes by [2+2] Cycloaddition of Alkenes and Allenoates.(-)-海罂粟烯 E 的合成：通过烯烃和丙二烯酸酯的 [2+2] 环加成反应构建偕二甲基-环丁烷。
Angew Chem Int Ed Engl. 2018 Apr 16;57(17):4647-4651. doi: 10.1002/anie.201801110. Epub 2018 Mar 24.
3
ORGANIC CHEMISTRY. Iron-catalyzed intermolecular [2+2] cycloadditions of unactivated alkenes.有机化学。铁催化的非活化烯烃的分子间[2+2]环加成反应。
Science. 2015 Aug 28;349(6251):960-3. doi: 10.1126/science.aac7440.
4
Lewis Acid-Promoted [2 + 2] Cycloadditions of Allenes and Ketenes: Versatile Methods for Natural Product Synthesis.路易斯酸促进的丙二烯与乙烯酮的[2 + 2]环加成反应：天然产物合成的通用方法
Acc Chem Res. 2023 Aug 15;56(16):2253-2264. doi: 10.1021/acs.accounts.3c00334. Epub 2023 Aug 4.
5
Enantioselective Total Synthesis of [3]-Ladderanol through Late-Stage Organocatalytic Desymmetrization.通过后期有机催化去对称化实现[3]-梯烷醇的对映选择性全合成。
Angew Chem Int Ed Engl. 2022 Jun 13;61(24):e202201584. doi: 10.1002/anie.202201584. Epub 2022 Apr 12.
6
Intramolecular Chirality Transfer [2 + 2] Cycloadditions of Allenoates and Alkenes.分子内手性转移[2+2]环加成反应：丙二烯酸酯和烯烃的反应
Org Lett. 2017 Jul 21;19(14):3703-3706. doi: 10.1021/acs.orglett.7b01420. Epub 2017 Jul 7.
7
Chemically induced anion radical cycloadditions: intramolecular cyclobutanation of bis(enones) via homogeneous electron transfer.化学诱导的阴离子自由基环加成反应：通过均相电子转移实现双烯酮的分子内环丁烷化反应
J Am Chem Soc. 2004 Feb 18;126(6):1634-5. doi: 10.1021/ja030543j.
8
Olefin-Supported Cationic Copper Catalysts for Photochemical Synthesis of Structurally Complex Cyclobutanes.用于光化学合成结构复杂的环丁烷的烯烃负载的阳离子铜催化剂。
Angew Chem Int Ed Engl. 2021 Feb 19;60(8):3989-3993. doi: 10.1002/anie.202013067. Epub 2020 Dec 29.
9
Diastereo- and Enantioselective Formal [3 + 2] Cycloaddition of Cyclopropyl Ketones and Alkenes via Ti-Catalyzed Radical Redox Relay.通过钛催化的自由基氧化还原接力反应实现环丙基酮和烯烃的非对映选择性和对映选择性[3 + 2]环加成。
J Am Chem Soc. 2018 Mar 14;140(10):3514-3517. doi: 10.1021/jacs.7b13710. Epub 2018 Feb 27.
10
Organocatalytic formal [2+2] cycloaddition initiated by vinylogous Friedel-Crafts alkylation: enantioselective synthesis of substituted cyclobutane derivatives.有机催化的形式 [2+2] 环加成引发的烯丙基 Friedel-Crafts 烷基化：取代环丁烷衍生物的对映选择性合成。
Chem Commun (Camb). 2013 May 21;49(41):4625-7. doi: 10.1039/c3cc41785a. Epub 2013 Apr 11.
引用本文的文献
1
Recent advances in the application of [2 + 2] cycloaddition in the chemical synthesis of cyclobutane-containing natural products.[2+2]环加成反应在含环丁烷天然产物化学合成中的应用新进展。
Nat Prod Bioprospect. 2024 Jun 11;14(1):37. doi: 10.1007/s13659-024-00457-9.
2
Tandem Isomerization/α,β-Site-Selective and Enantioselective Addition Reactions of -(3-Butynoyl)-3,5-dimethylpyrazole Induced by Chiral π-Cu(II) Catalysts.手性π-Cu(II)催化剂诱导的-(3-丁炔酰基)-3,5-二甲基吡唑的串联异构化/α,β-位点选择性及对映选择性加成反应
J Am Chem Soc. 2023 Dec 13;145(49):27080-27088. doi: 10.1021/jacs.3c10820. Epub 2023 Nov 30.
3
Lewis Acid-Promoted [2 + 2] Cycloadditions of Allenes and Ketenes: Versatile Methods for Natural Product Synthesis.路易斯酸促进的丙二烯与乙烯酮的[2 + 2]环加成反应：天然产物合成的通用方法
Acc Chem Res. 2023 Aug 15;56(16):2253-2264. doi: 10.1021/acs.accounts.3c00334. Epub 2023 Aug 4.
4
Stereoselective [2+2]-Cycloadditions of chiral allenic ketones and alkenes: Applications towards the synthesis of benzocyclobutenes and endiandric acids.手性联烯酮与烯烃的立体选择性[2+2]环加成反应：在苯并环丁烯和内型双环二烯酸合成中的应用
Tetrahedron. 2022 Sep 10;122. doi: 10.1016/j.tet.2022.132932. Epub 2022 Aug 8.
5
Unveiling the Chemistry and Synthetic Potential of Catalytic Cycloaddition Reaction of Allenes: A Review.揭开烯丙基催化环加成反应的化学与合成潜力：综述。
Molecules. 2023 Jan 10;28(2):704. doi: 10.3390/molecules28020704.
6
[2]-Ladderanes as isosteres for meta-substituted aromatic rings and rigidified cyclohexanes.[2]- ladderanes 作为间位取代芳烃和刚性环己烷的等排体。
Nat Commun. 2022 Oct 13;13(1):6056. doi: 10.1038/s41467-022-33827-3.
7
Preparation and Synthetic Applications of Five-to-Seven-Membered Cyclic α-Diazo Monocarbonyl Compounds.五至七元环α-重氮单羰基化合物的制备及合成应用。
Molecules. 2022 Mar 21;27(6):2030. doi: 10.3390/molecules27062030.
8
Total Synthesis and Anti-Inflammatory Bioactivity of (-)-Majusculoic Acid and Its Derivatives.(-)-大马酮酸及其衍生物的全合成及抗炎生物活性。
Mar Drugs. 2021 May 21;19(6):288. doi: 10.3390/md19060288.
9
Ladderane Natural Products: From the Ground Up. ladderane 天然产物：从基础开始。
Chemistry. 2021 Jan 7;27(2):565-576. doi: 10.1002/chem.202002866. Epub 2020 Oct 14.
10
Thioallenoates in Catalytic Enantioselective [2+2]-Cycloadditions with Unactivated Alkenes.硫代烯丙酸酯与未活化烯烃的催化对映选择性[2+2]环加成反应
Tetrahedron. 2019 Jun 14;75(24):3265-3271. doi: 10.1016/j.tet.2019.04.028. Epub 2019 Apr 25.
本文引用的文献
1
Intramolecular Chirality Transfer [2 + 2] Cycloadditions of Allenoates and Alkenes.分子内手性转移[2+2]环加成反应：丙二烯酸酯和烯烃的反应
Org Lett. 2017 Jul 21;19(14):3703-3706. doi: 10.1021/acs.orglett.7b01420. Epub 2017 Jul 7.
2
Chemical Synthesis and Self-Assembly of a Ladderane Phospholipid. ladderane 磷脂的化学合成与自组装。
J Am Chem Soc. 2016 Dec 14;138(49):15845-15848. doi: 10.1021/jacs.6b10706. Epub 2016 Nov 29.
3
Nature Utilizes Unusual High London Dispersion Interactions for Compact Membranes Composed of Molecular Ladders.自然界利用不寻常的高伦敦色散相互作用来形成由分子梯组成的致密膜。
J Chem Theory Comput. 2014 Mar 11;10(3):1353-8. doi: 10.1021/ct5000499. Epub 2014 Feb 24.
4
Cyclobutane and cyclobutene synthesis: catalytic enantioselective [2+2] cycloadditions.环丁烷和环丁烯的合成：催化对映选择性[2+2]环加成反应。
Angew Chem Int Ed Engl. 2015 Oct 5;54(41):11918-28. doi: 10.1002/anie.201502815. Epub 2015 Sep 2.
5
Stereoselective nickel-catalyzed [2+2] cycloadditions of ene-allenes.立体选择性镍催化的烯丙基烯的[2+2]环加成反应。
Angew Chem Int Ed Engl. 2015 Apr 27;54(18):5447-50. doi: 10.1002/anie.201411737. Epub 2015 Mar 10.
6
Catalytic enantioselective allenoate-alkene [2 + 2] cycloadditions.催化对映选择性丙二烯酸盐-烯烃 [2 + 2] 环加成反应。
J Am Chem Soc. 2015 Mar 18;137(10):3482-5. doi: 10.1021/jacs.5b00563. Epub 2015 Mar 10.
7
Insights into the role of cyclic ladderane lipids in bacteria from computer simulations.通过计算机模拟深入了解环状梯形烷脂质在细菌中的作用。
Chem Phys Lipids. 2014 Jul;181:76-82. doi: 10.1016/j.chemphyslip.2014.04.002. Epub 2014 Apr 13.
8
Ketenes and other cumulenes as reactive intermediates.作为反应中间体的烯酮和其他累积多烯。
Chem Rev. 2013 Sep 11;113(9):7287-342. doi: 10.1021/cr3005263. Epub 2013 Jun 14.
9
Design and Preparation of New Palladium Precatalysts for C-C and C-N Cross-Coupling Reactions.用于碳-碳和碳-氮交叉偶联反应的新型钯预催化剂的设计与制备
Chem Sci. 2013;4:916-920. doi: 10.1039/C2SC20903A.
10
How to make a living from anaerobic ammonium oxidation.如何从厌氧氨氧化中获利。
FEMS Microbiol Rev. 2013 May;37(3):428-61. doi: 10.1111/1574-6976.12014. Epub 2013 Jan 21.
Zotero 插件