ACS Publications. Most Trusted. Most Cited. Most Read
Total Synthesis and Structure Revision of (+)-Lancilactone C

OR SEARCH CITATIONS

My Activity
Publications

Figure 1Loading Img
Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Am. Chem. Soc. 2023, 145, 27, 14587-14591
    Communication

    Total Synthesis and Structure Revision of (+)-Lancilactone C
    Click to copy article linkArticle link copied!

    Other Access OptionsSupporting Information (1)

    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2023, 145, 27, 14587–14591
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jacs.3c04124
    Published June 16, 2023
    Copyright © 2023 American Chemical Society
    Request reuse permissions

    Abstract

    Click to copy section linkSection link copied!
    Abstract Image

    Lancilactone C is a tricyclic triterpenoid that inhibits human immunodeficiency virus (HIV) replication in H9 lymphocytes with no cytotoxicity. Its tricyclic skeleton comprises trans-dimethylbicyclo[4.3.0]nonane and 7-isopropylenecyclohepta-1,3,5-triene. The latter unique structure, in which all carbon atoms are sp2 hybridized, is not found in other triterpenoids and needs to be verified synthetically. Herein, we have accomplished the first total synthesis of lancilactone C (proposed structure) by developing a new domino [4 + 3] cycloaddition reaction involving oxidation, Diels–Alder reaction, elimination, and electrocyclization. We have also revised the structure based on the total synthesis of lancilactone C according to its plausible biosynthetic pathway.

    Copyright © 2023 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/jacs.3c04124.

    • Additional experimental details, experimental procedures, spectroscopic data, and 1H, 13C, and 2D NMR spectra. (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 5 publications.

    1. Jiang-Li Huang, Kun Li, Tong-Ling Cha, Dashan Li, Wen-Jing Wang, Li-Dong Shao. Recent advances in skeletal construction strategies and late-stage functionalization in the synthesis of natural triterpenoids. Tetrahedron 2025, 180 , 134666. https://doi.org/10.1016/j.tet.2025.134666
    2. Ruyi Chen, Yanlin Liu, Hanfeng Ding. Recent advances on electrocyclic reactions in complex natural product synthesis: an update. Organic Chemistry Frontiers 2025, 12 (7) , 2415-2438. https://doi.org/10.1039/D4QO02276A
    3. Anitesh Rana, Anupam Mishra, Satish K. Awasthi. Recent advancements in the chemistry of Diels–Alder reaction for total synthesis of natural products: a comprehensive review (2020–2023). RSC Advances 2025, 15 (6) , 4496-4525. https://doi.org/10.1039/D4RA07989B
    4. Yan-Fei Liu, Shi-Shan Yu. Survey of natural products reported by Asian research groups in 2023. Journal of Asian Natural Products Research 2024, 26 (12) , 1389-1404. https://doi.org/10.1080/10286020.2024.2412762
    5. . Total Synthesis of (+)-Lancilactone C. Synfacts 2023, 0960. https://doi.org/10.1055/s-0042-1752779
    Download PDF
    Go to Journal of the American Chemical Society
    Get e-Alerts
    Get e-Alerts

    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2023, 145, 27, 14587–14591
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jacs.3c04124
    Published June 16, 2023
    Copyright © 2023 American Chemical Society
    Request reuse permissions

    Article Views

    12k

    Altmetric

    -

    Citations

    5
    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.