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Site-Selective Functionalization of Linear Diterpenoids through U-Shaped Folding in a Confined Artificial Cavity

  • Hiroki Takezawa*
    Hiroki Takezawa
    Department of Applied Chemistry, School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-8656, Japan
    *[email protected]
  • Tomoya Kanda
    Tomoya Kanda
    Department of Applied Chemistry, School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-8656, Japan
    More by Tomoya Kanda
  • Hikaru Nanjo
    Hikaru Nanjo
    Department of Applied Chemistry, School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-8656, Japan
    More by Hikaru Nanjo
  • , and 
  • Makoto Fujita*
    Makoto Fujita
    Department of Applied Chemistry, School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-8656, Japan
    *[email protected]
Cite this: J. Am. Chem. Soc. 2019, 141, 13, 5112–5115
Publication Date (Web):March 15, 2019
https://doi.org/10.1021/jacs.9b00131
Copyright © 2019 American Chemical Society

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    Abstract

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    Even flexible linear substrates are conformationally fixed within the hydrophobic confined cavities of enzymes. This enables preorganization of the substrates and their positioning in close proximity to the active center to facilitate stereo- and site-selective reactions. Here, we demonstrate the site-selective electrophilic addition of linear diterpenoids within a self-assembled coordination cage. The reactions proceed through folding of the linear substrates into a U-shaped conformation, which results in noncovalent protection of internal C═C bonds to enhance the site selectivity.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/jacs.9b00131.

    • Experimental procedures, physical properties, crystallographic data (PDF)

    • Crystallographic data for 1·2b·pyrene (CIF)

    • Crystallographic data for 1·2d·pyrene (CIF)

    • Crystallographic data for 1·2c·pyrene (CIF)

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    14. Edmundo G. Percástegui, Tanya K. Ronson, Jonathan R. Nitschke. Design and Applications of Water-Soluble Coordination Cages. Chemical Reviews 2020, 120 (24) , 13480-13544. https://doi.org/10.1021/acs.chemrev.0c00672
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    23. Trandon A. Bender, Robert G. Bergman, Kenneth N. Raymond, F. Dean Toste. A Supramolecular Strategy for Selective Catalytic Hydrogenation Independent of Remote Chain Length. Journal of the American Chemical Society 2019, 141 (30) , 11806-11810. https://doi.org/10.1021/jacs.9b05604
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    37. P. Kočovský. Addition Reactions: Polar Addition. 2023, 345-471. https://doi.org/10.1002/9781119608288.ch10
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    41. Shao‐Chuan Li, Li‐Xuan Cai, Maochun Hong, Qihui Chen, Qing‐Fu Sun. Combinatorial Self‐Assembly of Coordination Cages with Systematically Fine‐Tuned Cavities for Efficient Co‐Encapsulation and Catalysis. Angewandte Chemie International Edition 2022, 61 (33) https://doi.org/10.1002/anie.202204732
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    47. C. Li, A.-D. Manick, J.-P. Dutasta, X. Bugaut, B. Chatelet, A. Martinez. Frustrated behavior of Lewis/Brønsted pairs inside molecular cages. Organic Chemistry Frontiers 2022, 9 (7) , 1826-1836. https://doi.org/10.1039/D2QO00011C
    48. Qiaosheng Li, Defa Gu, Dongdong Yu, Yuzhou Liu. Caged Iridium Catalyst for Hydrosilylation of Alkynes with High Site Selectivity. ChemCatChem 2022, 14 (5) https://doi.org/10.1002/cctc.202101727
    49. Ming‐Hao Du, Su‐Hui Xu, Guan‐Jun Li, Han Xu, Yang Lin, Wei‐Dong Liu, La‐Sheng Long, Lan‐Sun Zheng, Xiang‐Jian Kong. Modification of Multi‐Component Building Blocks for Assembling Giant Chiral Lanthanide‐Titanium Molecular Rings. Angewandte Chemie 2022, 134 (8) https://doi.org/10.1002/ange.202116296
    50. Ming‐Hao Du, Su‐Hui Xu, Guan‐Jun Li, Han Xu, Yang Lin, Wei‐Dong Liu, La‐Sheng Long, Lan‐Sun Zheng, Xiang‐Jian Kong. Modification of Multi‐Component Building Blocks for Assembling Giant Chiral Lanthanide‐Titanium Molecular Rings. Angewandte Chemie International Edition 2022, 61 (8) https://doi.org/10.1002/anie.202116296
    51. Yang Jiao, Xiao-Yang Chen, J. Fraser Stoddart. Weak bonding strategies for achieving regio- and site-selective transformations. Chem 2022, 8 (2) , 414-438. https://doi.org/10.1016/j.chempr.2021.12.012
    52. Yan Sun, Chongyi Chen, Fengmin Zhang, Shaowei Jiang, Peter J. Stang. Pt Metallacage-based centimeter films for smart emissive poly(N-isopropylacrylamide) hydrogel devices. Materials Chemistry and Physics 2022, 277 , 125544. https://doi.org/10.1016/j.matchemphys.2021.125544
    53. Ming-Jie Yan, Sheng-Li Huang, Guo-Yu Yang. Dual-AIEgens in one organoplatinum( ii ) metallaprism: photoluminescence exploration. Dalton Transactions 2022, 51 (3) , 842-846. https://doi.org/10.1039/D1DT03919A
    54. Rui Wang, Yang Yu. Site-selective reactions mediated by molecular containers. Beilstein Journal of Organic Chemistry 2022, 18 , 309-324. https://doi.org/10.3762/bjoc.18.35
    55. Hiroki Takezawa, Makoto Fujita. Molecular Confinement Effects by Self-Assembled Coordination Cages. Bulletin of the Chemical Society of Japan 2021, 94 (10) , 2351-2369. https://doi.org/10.1246/bcsj.20210273
    56. Yan Sun, Peter J. Stang. Metallacycles, metallacages, and their aggregate/optical behavior. Aggregate 2021, 2 (5) https://doi.org/10.1002/agt2.94
    57. Igor S. Antipin, Mikhail V. Alfimov, Vladimir V. Arslanov, Vladimir A. Burilov, Sergey Z. Vatsadze, Yan Z. Voloshin, Konstantin P. Volcho, Valery V. Gorbatchuk, Yulia G. Gorbunova, Sergey P. Gromov, Semyon V. Dudkin, Sergei Yu. Zaitsev, Lucia Ya. Zakharova, Marat A. Ziganshin, Anna V. Zolotukhina, Maria A. Kalinina, Eduard A. Karakhanov, Ruslan R. Kashapov, Oskar I. Koifman, Alexander I. Konovalov, Vladimir S. Korenev, Anton L. Maksimov, Nugzar Zh. Mamardashvili, Galina M. Mamardashvili, Alexander G. Martynov, Asiya R. Mustafina, Ramil I. Nugmanov, Alexander S. Ovsyannikov, Pavel L. Padnya, Andrei S. Potapov, Sofiya L. Selektor, Maxim N. Sokolov, Svetlana E. Solovieva, Ivan I. Stoikov, Pavel A. Stuzhin, Evgenii V. Suslov, Evgeny N. Ushakov, Vladimir P. Fedin, Svetlana V. Fedorenko, Olga A. Fedorova, Yury V. Fedorov, Sergei N. Chvalun, Aslan Yu. Tsivadze, Sergei N. Shtykov, Dmitriy N. Shurpik, Maxim A. Shcherbina, Luidmila S. Yakimova. Functional supramolecular systems: design and applications. Russian Chemical Reviews 2021, 90 (8) , 895-1107. https://doi.org/10.1070/RCR5011
    58. Xiaoyu Hao, Tian‐Ren Li, Hao Chen, Andrea Gini, Xiang Zhang, Stéphane Rosset, Clément Mazet, Konrad Tiefenbacher, Stefan Matile. Bioinspired Ether Cyclizations within a π‐Basic Capsule Compared to Autocatalysis on π‐Acidic Surfaces and Pnictogen‐Bonding Catalysts. Chemistry – A European Journal 2021, 27 (47) , 12215-12223. https://doi.org/10.1002/chem.202101548
    59. Shohei Tashiro, Wei He, Ryunosuke Hayashi, Yingjie Lin, Mitsuhiko Shionoya. Site-selective binding of terpenoids within a confined space of metal–macrocycle framework: substrate-specific promotion or inhibition of cyclization reactions. Organic Chemistry Frontiers 2021, 8 (15) , 4071-4077. https://doi.org/10.1039/D1QO00750E
    60. Giorgio Olivo, Giorgio Capocasa, Daniele Del Giudice, Osvaldo Lanzalunga, Stefano Di Stefano. New horizons for catalysis disclosed by supramolecular chemistry. Chemical Society Reviews 2021, 50 (13) , 7681-7724. https://doi.org/10.1039/D1CS00175B
    61. Qingqing Sun, Luis Escobar, Pablo Ballester. Hydrolysis of Aliphatic Bis ‐isonitriles in the Presence of a Polar Super Aryl‐Extended Calix[4]pyrrole Container. Angewandte Chemie 2021, 133 (18) , 10447-10453. https://doi.org/10.1002/ange.202101499
    62. Qingqing Sun, Luis Escobar, Pablo Ballester. Hydrolysis of Aliphatic Bis ‐isonitriles in the Presence of a Polar Super Aryl‐Extended Calix[4]pyrrole Container. Angewandte Chemie International Edition 2021, 60 (18) , 10359-10365. https://doi.org/10.1002/anie.202101499
    63. Yu Zhang, Qianqian Yang, Jingjing Lu, Mei Guo, Xiao-Lei Li, Jinkui Tang. Heterometallic {DyIII2FeII2} grids with slow magnetic relaxation and spin crossover. Inorganic Chemistry Frontiers 2021, 8 (7) , 1779-1787. https://doi.org/10.1039/D0QI01471K
    64. Isha Mishra, Mamina Bhol, Palanisamy Kalimuthu, Malaichamy Sathiyendiran. Emerging Spacers‐Based Ligands for Supramolecular Coordination Complexes. The Chemical Record 2021, 21 (3) , 594-614. https://doi.org/10.1002/tcr.202000150
    65. Valentina Dichiarante, Claudia Pigliacelli, Pierangelo Metrangolo, Francesca Baldelli Bombelli. Confined space design by nanoparticle self-assembly. Chemical Science 2021, 12 (5) , 1632-1646. https://doi.org/10.1039/D0SC05697A
    66. Mariko Morimoto, Stephen M. Bierschenk, Kay T. Xia, Robert G. Bergman, Kenneth N. Raymond, F. Dean Toste. Advances in supramolecular host-mediated reactivity. Nature Catalysis 2020, 3 (12) , 969-984. https://doi.org/10.1038/s41929-020-00528-3
    67. Benjamin Mitschke, Mathias Turberg, Benjamin List. Confinement as a Unifying Element in Selective Catalysis. Chem 2020, 6 (10) , 2515-2532. https://doi.org/10.1016/j.chempr.2020.09.007
    68. Sarita Yadav, Palanisamy Kannan, Guanyinsheng Qiu. Cavity-based applications of metallo-supramolecular coordination cages (MSCCs). Organic Chemistry Frontiers 2020, 7 (18) , 2842-2872. https://doi.org/10.1039/D0QO00681E
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    70. Kuo Zhang, Duo Xu, Li Zhao, Zhong-Yuan Lu. Proper adsorptive confinement for efficient production of cyclic polymers: a dissipative particle dynamics study. Physical Chemistry Chemical Physics 2020, 22 (33) , 18703-18710. https://doi.org/10.1039/D0CP02210A
    71. Kaiya Wang, Jacobs H. Jordan, Xiao‐Yu Hu, Leyong Wang. Supramolecular Strategies for Controlling Reactivity within Confined Nanospaces. Angewandte Chemie 2020, 132 (33) , 13816-13825. https://doi.org/10.1002/ange.202000045
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    73. Yunhe Jin, Qingqing Zhang, Yongqiang Zhang, Chunying Duan. Electron transfer in the confined environments of metal–organic coordination supramolecular systems. Chemical Society Reviews 2020, 49 (15) , 5561-5600. https://doi.org/10.1039/C9CS00917E
    74. Ben S. Pilgrim, Neil R. Champness. Metal‐Organic Frameworks and Metal‐Organic Cages – A Perspective. ChemPlusChem 2020, 85 (8) , 1842-1856. https://doi.org/10.1002/cplu.202000408
    75. Giorgio Olivo, Giorgio Capocasa, Barbara Ticconi, Osvaldo Lanzalunga, Stefano Di Stefano, Miquel Costas. Predictable Selectivity in Remote C−H Oxidation of Steroids: Analysis of Substrate Binding Mode. Angewandte Chemie 2020, 132 (31) , 12803-12808. https://doi.org/10.1002/ange.202003078
    76. Giorgio Olivo, Giorgio Capocasa, Barbara Ticconi, Osvaldo Lanzalunga, Stefano Di Stefano, Miquel Costas. Predictable Selectivity in Remote C−H Oxidation of Steroids: Analysis of Substrate Binding Mode. Angewandte Chemie International Edition 2020, 59 (31) , 12703-12708. https://doi.org/10.1002/anie.202003078
    77. Shin-ichiro Noro, Yu Song, Yutaro Tanimoto, Yuh Hijikata, Kazuya Kubo, Takayoshi Nakamura. Controlling the gate-sorption properties of solid solutions of Werner complexes by varying component ratios. Dalton Transactions 2020, 49 (27) , 9438-9443. https://doi.org/10.1039/D0DT01355B
    78. Jinqiao Dong, Yutong Pan, Heng Wang, Kuiwei Yang, Lingmei Liu, Zhiwei Qiao, Yi Di Yuan, Shing Bo Peh, Jian Zhang, Leilei Shi, Hong Liang, Yu Han, Xiaopeng Li, Jianwen Jiang, Bin Liu, Dan Zhao. Self‐Assembly of Highly Stable Zirconium(IV) Coordination Cages with Aggregation Induced Emission Molecular Rotors for Live‐Cell Imaging. Angewandte Chemie 2020, 132 (25) , 10237-10245. https://doi.org/10.1002/ange.201915199
    79. Jinqiao Dong, Yutong Pan, Heng Wang, Kuiwei Yang, Lingmei Liu, Zhiwei Qiao, Yi Di Yuan, Shing Bo Peh, Jian Zhang, Leilei Shi, Hong Liang, Yu Han, Xiaopeng Li, Jianwen Jiang, Bin Liu, Dan Zhao. Self‐Assembly of Highly Stable Zirconium(IV) Coordination Cages with Aggregation Induced Emission Molecular Rotors for Live‐Cell Imaging. Angewandte Chemie International Edition 2020, 59 (25) , 10151-10159. https://doi.org/10.1002/anie.201915199
    80. Yang Yu, Ji-Min Yang, Julius Rebek. Molecules in Confined Spaces: Reactivities and Possibilities in Cavitands. Chem 2020, 6 (6) , 1265-1274. https://doi.org/10.1016/j.chempr.2020.04.014
    81. Mona Sharafi, Kyle T. McKay, Monika Ivancic, Dillon R. McCarthy, Natavan Dudkina, Kyle E. Murphy, Sinu C. Rajappan, Joseph P. Campbell, Yuxiang Shen, Appala Raju Badireddy, Jianing Li, Severin T. Schneebeli. Size-Selective Catalytic Polymer Acylation with a Molecular Tetrahedron. Chem 2020, 6 (6) , 1469-1494. https://doi.org/10.1016/j.chempr.2020.05.011
    82. Sota Yonemura, Takashi Nakamura, Tatsuya Nabeshima. Threading/Folding Recognition Modes of Phosphodiesters by a p -Nitrophenylamide Cyclodextrin Derivative. Chemistry Letters 2020, 49 (5) , 493-496. https://doi.org/10.1246/cl.200085
    83. Angela B. Grommet, Moran Feller, Rafal Klajn. Chemical reactivity under nanoconfinement. Nature Nanotechnology 2020, 15 (4) , 256-271. https://doi.org/10.1038/s41565-020-0652-2
    84. Rebecca J. Severinsen, Gareth J. Rowlands, Paul G. Plieger. Coordination cages in catalysis. Journal of Inclusion Phenomena and Macrocyclic Chemistry 2020, 96 (1-2) , 29-42. https://doi.org/10.1007/s10847-019-00964-0
    85. Sijia Zheng, Liang Zhao, Jianwei Wei, Cheng He, Guangzhou Liu, Chunying Duan. A new cobalt triangular prism supramolecular flask: Encapsulation of a quinhydrone cofactor for hydrogenation of nitroarenes with high selectivity and efficiency. Inorganic Chemistry Communications 2019, 109 , 107558. https://doi.org/10.1016/j.inoche.2019.107558
    86. Venkatachalam Angamuthu, Faiz-Ur Rahman, Manuel Petroselli, Yongsheng Li, Yang Yu, Julius Rebek. Mono epoxidation of α,ω-dienes using NBS in a water-soluble cavitand. Organic Chemistry Frontiers 2019, 6 (18) , 3220-3223. https://doi.org/10.1039/C9QO00849G
    87. William Cullen, Hiroki Takezawa, Makoto Fujita. Demethylenation of Cyclopropanes via Photoinduced Guest‐to‐Host Electron Transfer in an M 6 L 4 Cage. Angewandte Chemie 2019, 131 (27) , 9269-9271. https://doi.org/10.1002/ange.201904752
    88. William Cullen, Hiroki Takezawa, Makoto Fujita. Demethylenation of Cyclopropanes via Photoinduced Guest‐to‐Host Electron Transfer in an M 6 L 4 Cage. Angewandte Chemie International Edition 2019, 58 (27) , 9171-9173. https://doi.org/10.1002/anie.201904752

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