• Login
    View Item 
    •   Home
    • Office of Sponsored Research (OSR)
    • KAUST Funded Research
    • Publications Acknowledging KAUST Support
    • View Item
    •   Home
    • Office of Sponsored Research (OSR)
    • KAUST Funded Research
    • Publications Acknowledging KAUST Support
    • View Item
    JavaScript is disabled for your browser. Some features of this site may not work without it.

    Browse

    All of KAUSTCommunitiesIssue DateSubmit DateThis CollectionIssue DateSubmit Date

    My Account

    Login

    Quick Links

    Open Access PolicyORCID LibguideTheses and Dissertations LibguideSubmit an Item

    Statistics

    Display statistics

    Total Syntheses of Cyanthiwigins B, F, and G

    • CSV
    • RefMan
    • EndNote
    • BibTex
    • RefWorks
    Type
    Article
    Authors
    Enquist, John A.
    Virgil, Scott C.
    Stoltz, Brian M.
    KAUST Grant Number
    KUS-11-006-02
    Date
    2011-07-18
    Online Publication Date
    2011-07-18
    Print Publication Date
    2011-08-29
    Permanent link to this record
    http://hdl.handle.net/10754/600040
    
    Metadata
    Show full item record
    Abstract
    A concise and versatile approach toward the preparation of the cyanthiwigin family of cyathane natural products is described. By leveraging a unique double asymmetric catalytic alkylation procedure it is possible to quickly establish two of the most critical stereocenters of the cyanthiwigin framework with high levels of selectivity and expediency. The synthetic route additionally employs both a tandem ring-closing cross-metathesis reaction, and an aldehyde-olefin radical cyclization process, in order to rapidly arrive at the tricyclic cyathane core of the cyanthiwigin molecules. From this unifying intermediate, the preparations of cyanthiwigins B, F, and G are attained swiftly and without the need for protecting groups.
    Citation
    Enquist JA, Virgil SC, Stoltz BM (2011) Total Syntheses of Cyanthiwigins B, F, and G. Chem Eur J 17: 9957–9969. Available: http://dx.doi.org/10.1002/chem.201100425.
    Sponsors
    This publication is based on work supported by Award No. KUS-11-006-02, made by King Abdullah University of Science and Technology (KAUST). The authors wish to thank NIH-NIGMS (R01M080269-01), Amgen, Abbott, Boehringer Ingelheim, Merck, and Bristol-Myers Squibbs, GlaxoSmithKline, Johnson and Johnson, Amgen, Merck Research Laboratories, Pfizer, Novartis, Roche, Abbott Laboratories, Boehringer-Ingelheim, AstraZeneca, and Caltech for financial support. We also wish to thank Dr. M. W. Day and Mr. L. M. Henling for X-ray crystallographic expertise, Dr. Andrew Harned, Dr. David White, Daniel Caspi, and J. T. Mohr for helpful discussions, and Professor Mark T. Hamann for authentic samples and spectra of cyanthiwigins B, F, and G. Ruthenium olefin metathesis catalysts were generously donated by Materia.
    Publisher
    Wiley
    Journal
    Chemistry - A European Journal
    DOI
    10.1002/chem.201100425
    PubMed ID
    21769952
    PubMed Central ID
    PMC3365662
    ae974a485f413a2113503eed53cd6c53
    10.1002/chem.201100425
    Scopus Count
    Collections
    Publications Acknowledging KAUST Support

    entitlement

    Related articles

    • Total synthesis of cyanthiwigins A, C, G, and H.
    • Authors: Wang C, Wang D, Gao S
    • Issue date: 2013 Sep 6
    • Asymmetric synthesis of the tricyclic core of NGF-inducing cyathane diterpenes via a transition-metal-catalyzed [5 + 2] cycloaddition.
    • Authors: Wender PA, Bi FC, Brodney MA, Gosselin F
    • Issue date: 2001 Jun 28
    • The total synthesis of (-)-cyanthiwigin F by means of double catalytic enantioselective alkylation.
    • Authors: Enquist JA Jr, Stoltz BM
    • Issue date: 2008 Jun 26
    • Total synthesis of (+)-cyanthiwigin U.
    • Authors: Pfeiffer MW, Phillips AJ
    • Issue date: 2005 Apr 20
    • Enantioselective total synthesis of briarellins E and F: the first total syntheses of briarellin diterpenes.
    • Authors: Corminboeuf O, Overman LE, Pennington LD
    • Issue date: 2003 Jun 4
    DSpace software copyright © 2002-2023  DuraSpace
    Quick Guide | Contact Us | KAUST University Library
    Open Repository is a service hosted by 
    Atmire NV
     

    Export search results

    The export option will allow you to export the current search results of the entered query to a file. Different formats are available for download. To export the items, click on the button corresponding with the preferred download format.

    By default, clicking on the export buttons will result in a download of the allowed maximum amount of items. For anonymous users the allowed maximum amount is 50 search results.

    To select a subset of the search results, click "Selective Export" button and make a selection of the items you want to export. The amount of items that can be exported at once is similarly restricted as the full export.

    After making a selection, click one of the export format buttons. The amount of items that will be exported is indicated in the bubble next to export format.