ACS Publications. Most Trusted. Most Cited. Most Read
My Activity
CONTENT TYPES

Figure 1Loading Img

Total Synthesis of (+)-Shearilicine

  • Daria E. Kim
    Daria E. Kim
    Department of Chemistry, Yale University, 225 Prospect Street, New Haven, Connecticut 06520-8107, United States
    More by Daria E. Kim
  • Yingchuan Zhu
    Yingchuan Zhu
    Department of Chemistry, Yale University, 225 Prospect Street, New Haven, Connecticut 06520-8107, United States
  • Shingo Harada
    Shingo Harada
    Department of Chemistry, Yale University, 225 Prospect Street, New Haven, Connecticut 06520-8107, United States
    Graduate School of Pharmaceutical Sciences, Chiba University, Chiba 260-8675, Japan
  • Isaiah Aguilar
    Isaiah Aguilar
    Department of Chemistry, Yale University, 225 Prospect Street, New Haven, Connecticut 06520-8107, United States
  • Abbigayle E. Cuomo
    Abbigayle E. Cuomo
    Department of Chemistry, Yale University, 225 Prospect Street, New Haven, Connecticut 06520-8107, United States
  • Minghao Wang
    Minghao Wang
    Department of Chemistry, Yale University, 225 Prospect Street, New Haven, Connecticut 06520-8107, United States
    More by Minghao Wang
  • , and 
  • Timothy R. Newhouse*
    Timothy R. Newhouse
    Department of Chemistry, Yale University, 225 Prospect Street, New Haven, Connecticut 06520-8107, United States
    *[email protected]
Cite this: J. Am. Chem. Soc. 2023, 145, 8, 4394–4399
Publication Date (Web):February 15, 2023
https://doi.org/10.1021/jacs.2c13584
Copyright © 2023 American Chemical Society

    Article Views

    13697

    Altmetric

    -

    Citations

    -
    LEARN ABOUT THESE METRICS
    Other access options
    Supporting Info (1)»

    Abstract

    Abstract Image

    Herein we report the first total synthesis of the indole diterpenoid natural product shearilicine by an 11-step sequence via a generalizable precursor to the highly oxidized subclass of indole diterpenoids. A native chiral auxiliary strategy was employed to access the target molecule in an enantiospecific fashion. The formation of the key carbazole substructure was achieved through a mild intramolecular Heck cyclization, wherein a computational study revealed noncovalent substrate–ligand and ligand–ligand interactions that promoted migratory insertion.

    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. You can change your affiliated institution below.

    Supporting Information

    ARTICLE SECTIONS
    Jump To

    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/jacs.2c13584.

    • Discussions of general experimental details, synthesis methods, computational details, computational methods for attractive dispersion, and determining anion-ligand/substrate interactions, figures of NMR spectra, Gibbs free-energy profiles, and method to evaluate attractive dispersion interactions, and tables of comparison of synthetic and natural 1H and 13C NMR, Cartesian coordinates, and associated distances (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

    This article has not yet been cited by other publications.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    You’ve supercharged your research process with ACS and Mendeley!

    STEP 1:
    Click to create an ACS ID

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    MENDELEY PAIRING EXPIRED
    Your Mendeley pairing has expired. Please reconnect