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Stereoselective Synthesis of Conjugated Polyenes Based on Tethered Olefin Metathesis and Carbonyl Olefination: Application to the Total Synthesis of (+)-Bretonin B
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    Stereoselective Synthesis of Conjugated Polyenes Based on Tethered Olefin Metathesis and Carbonyl Olefination: Application to the Total Synthesis of (+)-Bretonin B
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2020, 85, 7, 5122–5130
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    https://doi.org/10.1021/acs.joc.0c00446
    Published March 12, 2020
    Copyright © 2020 American Chemical Society

    Abstract

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    The combination of a highly stereoselective tethered olefin metathesis reaction and a Julia–Kocienski olefination is presented as a strategy for the synthesis of conjugated polyenes with at least one Z-configured C═C bond. The strategy is exemplified by the synthesis of the marine natural product (+)-bretonin B.

    Copyright © 2020 American Chemical Society

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.joc.0c00446.

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    This article is cited by 4 publications.

    1. Jie Jack Li. Julia–Kocienski Olefinierung. 2024, 303-306. https://doi.org/10.1007/978-3-031-52850-7_75
    2. Capucine Jourdain de Muizon, Céline Moriou, Sylvain Petek, Merrick Ekins, Marthe Rousseau, Ali Al Mourabit. Isolation, Synthesis and Absolute Configuration of the Pericharaxins A and B, Epimeric Hydroxy-Polyene Glycerol Ethers from the Calcarean Sponge Pericharax heteroraphis. Marine Drugs 2022, 20 (10) , 635. https://doi.org/10.3390/md20100635
    3. Pulluparambil Xavier Thresia Rinu, Sankaran Radhika, Gopinathan Anilkumar. Recent Applications and Trends in the Julia‐Kocienski Olefination. ChemistrySelect 2022, 7 (31) https://doi.org/10.1002/slct.202200760
    4. Jie Jack Li. Julia–Kocienski Olefination. 2021, 288-290. https://doi.org/10.1007/978-3-030-50865-4_75

    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2020, 85, 7, 5122–5130
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.joc.0c00446
    Published March 12, 2020
    Copyright © 2020 American Chemical Society

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