ACS Publications. Most Trusted. Most Cited. Most Read
Total Synthesis of (−)-Zearalenone and (−)-Zearalanone: A Macrocyclization Strategy by Ni/Zr/Cr-Mediated Reductive Ketone Coupling

OR SEARCH CITATIONS

My Activity
Publications

Figure 1Loading Img
Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Org. Chem. 2024, 89, 18, 13800-13805
    Note

    Total Synthesis of (−)-Zearalenone and (−)-Zearalanone: A Macrocyclization Strategy by Ni/Zr/Cr-Mediated Reductive Ketone Coupling
    Click to copy article linkArticle link copied!

    Other Access OptionsSupporting Information (1)

    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2024, 89, 18, 13800–13805
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.joc.4c01793
    Published September 10, 2024
    Copyright © 2024 American Chemical Society
    Request reuse permissions

    Abstract

    Click to copy section linkSection link copied!
    Abstract Image

    The total synthesis of the resorcylic acid lactones (−)-zearalenone and (−)-zearalanone is described. Our synthetic strategy relies on Ni-, Zr-, and Cr-mediated intramolecular reductive ketone coupling to create 14-membered macrolactones. Notably, the use of CrCl2 in addition to Ni/Zr-mediated reductive ketone coupling conditions was key for the success of the macrocyclization.

    Copyright © 2024 American Chemical Society

    Subjects

    what are subjects

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. Add or change your institution or let them know you’d like them to include access.

    Supporting Information

    Click to copy section linkSection link copied!

    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.joc.4c01793.

    • Experimental procedures, characterization data, and NMR spectra of all newly synthesized compounds. (PDF)

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    Click to copy section linkSection link copied!
    Citation Statements
    Explore this article's citation statements on scite.ai
    powered by  Scite

    This article is cited by 1 publications.

    1. Ryoga Hashimoto, Kenta Kameda, Shoki Kuresawa, Tomoya Iwasaki, Toshiki Furutani, Mugen Yamawaki, Hirotsugu Suzuki, Yasuharu Yoshimi. Ring Expansion from 16‐Membered Macrocyclic Lactones Using Yamaguchi and Photoinduced Decarboxylative Radical Macrolactonization. Asian Journal of Organic Chemistry 2025, 14 (1) https://doi.org/10.1002/ajoc.202400560
    Download PDF
    Go to The Journal of Organic Chemistry
    Get e-Alerts
    Get e-Alerts

    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2024, 89, 18, 13800–13805
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.joc.4c01793
    Published September 10, 2024
    Copyright © 2024 American Chemical Society
    Request reuse permissions

    Article Views

    1790

    Altmetric

    -

    Citations

    1
    Learn about these metrics

    Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

    Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.

    The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.