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Synthesis of Novel Nucleoside Analogues Built on a Bicyclo[4.1.0]heptane Scaffold

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    Synthesis of Novel Nucleoside Analogues Built on a Bicyclo[4.1.0]heptane Scaffold
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    † Departament de Quı́mica, Universitat Autònoma de Barcelona, 08193 Bellaterra, Spain
    ‡ Rega Institute for Medical Research, Department of Microbiology and Immunology, Katholieke Universiteit Leuven, B-3000 Leuven, Belgium
    *E-mail for R.A.: [email protected]
    *E-mail for F.B.: [email protected]
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2015, 80, 19, 9495–9505
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    https://doi.org/10.1021/acs.joc.5b01413
    Published September 16, 2015
    Copyright © 2015 American Chemical Society
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    Abstract

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    A new class of carbocyclic nucleoside analogues built on a bicyclo[4.1.0]heptane scaffold, a perspective novel pseudosugar pattern, have been conceived as anti-HSV agents on the basis of initial protein–ligand docking studies. The asymmetric synthesis of a series of these compounds incorporating different nucleobases has been efficiently completed starting from 1,4-cyclohexanedione.

    Copyright © 2015 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.joc.5b01413.

    • Computational details, 1H and 13C NMR spectra of all new compounds, and 2D NMR spectra for compounds 12–15, 5, 18, 22, 28, and 2a–d (PDF)

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    This article is cited by 9 publications.

    1. Zheyuan Wang, Zhilin Song, Jun Huang, Zhen Yang. Total Synthesis of Penicibilaenes Enabled by a Tandem Double Conia-ene Type Reaction. Journal of the American Chemical Society 2024, 146 (7) , 4363-4368. https://doi.org/10.1021/jacs.3c14614
    2. Sergio Jurado, Ona Illa, Angel Álvarez-Larena, Christophe Pannecouque, Félix Busqué, Ramon Alibés. Conformationally Locked Carbocyclic Nucleosides Built on a 4′-Hydroxymethyl-3′-hydroxybicyclo[4.1.0]heptane Template. Stereoselective Synthesis and Antiviral Activity. The Journal of Organic Chemistry 2022, 87 (22) , 15166-15177. https://doi.org/10.1021/acs.joc.2c01661
    3. Nai-Chen Hsueh, Yu-Han Wang, Meng-Yang Chang. Sequential condensation and double desulfonylative cyclopropanation of 1,2-bis(sulfonylmethyl)arenes with 3-arylacroleins: access to biscyclopropane-fused tetralins. Organic & Biomolecular Chemistry 2023, 21 (6) , 1206-1221. https://doi.org/10.1039/D2OB02188A
    4. Sergio Jurado, Beatriz Domínguez-Pérez, Ona Illa, Jan Balzarini, Félix Busqué, Ramon Alibés. Enantiocontrolled Preparation of ϒ-Substituted Cyclohexenones: Synthesis and Kinase Activity Assays of Cyclopropyl-Fused Cyclohexane Nucleosides. International Journal of Molecular Sciences 2022, 23 (17) , 9704. https://doi.org/10.3390/ijms23179704
    5. Galal H. Elgemeie, Reham A. Mohamed-Ezzat. Synthetic strategies for purine nucleoside analogs. 2022, 221-301. https://doi.org/10.1016/B978-0-12-821783-2.00002-9
    6. Serghei Curlat. Recent Studies of (+)-3-Carene Transformations with the Retention of the Native Framework. Chemistry Journal of Moldova 2019, 14 (2) , 32-55. https://doi.org/10.19261/cjm.2019.616
    7. Macarena Eugui, Florencia Parpal, Andrés López Radcenco, Guillermo Moyna. Synthetic Methods for the Preparation of Norcarane Scaffolds. A Review. Organic Preparations and Procedures International 2018, 50 (3) , 260-287. https://doi.org/10.1080/00304948.2018.1462048
    8. Yuichi Yoshimura. Development of a Glycosylation Reaction: A Key to Accessing Structurally Unique Nucleosides. HETEROCYCLES 2017, 94 (9) , 1625. https://doi.org/10.3987/REV-17-865
    9. Shusuke Okamoto, Keita Kojiyama, Hiroki Tsujioka, Atsushi Sudo. Metal-free reductive coupling of CO and CN bonds driven by visible light: use of perylene as a simple photoredox catalyst. Chemical Communications 2016, 52 (76) , 11339-11342. https://doi.org/10.1039/C6CC05867A
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2015, 80, 19, 9495–9505
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.joc.5b01413
    Published September 16, 2015
    Copyright © 2015 American Chemical Society
    Request reuse permissions

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