An approach to the bicyclic C-5-C-17/C-19-C-20 (BC) portion of neoclerodane diterpenes by intramolecular Diels-Alder reaction

Yuzhou Wang, Victor Rogachev, Martin Wolter, Margit Gruner, Anne Jäger, Peter Metz

    Research output: Contribution to journalArticle

    5 Citations (Scopus)

    Abstract

    Using a highly diastereoselective intramolecular acrylate [4+2] cycloaddition as the key step, a short route from 3-furaldehyde to a bicyclic building block for the synthesis of neoclerodane diterpenes was developed. A first attempt featuring a conjugate methylation of a dienyl lactone failed, but a streamlined sequence using an all-encompassing intramolecular Diels-Alder reaction of a sterically congested 1,3-diene was successful. A highly diastereoselective intramolecular acrylate [4+2] cycloaddition of a sterically congested 1,3-diene served as the key step in a short synthesis of a BC building block for neoclerodane diterpenes.

    Original languageEnglish
    Pages (from-to)4083-4088
    Number of pages6
    JournalEuropean Journal of Organic Chemistry
    Volume2014
    Issue number19
    DOIs
    Publication statusPublished - 2014

    Fingerprint

    Diels-Alder reactions
    Cycloaddition
    Diterpenes
    cycloaddition
    dienes
    acrylates
    Furaldehyde
    methylation
    Methylation
    Lactones
    synthesis
    routes
    acrylic acid
    neoclerodane

    Keywords

    • Cross-coupling
    • Cycloaddition
    • Michael addition
    • Natural products
    • Terpenoids

    ASJC Scopus subject areas

    • Organic Chemistry
    • Physical and Theoretical Chemistry

    Cite this

    An approach to the bicyclic C-5-C-17/C-19-C-20 (BC) portion of neoclerodane diterpenes by intramolecular Diels-Alder reaction. / Wang, Yuzhou; Rogachev, Victor; Wolter, Martin; Gruner, Margit; Jäger, Anne; Metz, Peter.

    In: European Journal of Organic Chemistry, Vol. 2014, No. 19, 2014, p. 4083-4088.

    Research output: Contribution to journalArticle

    Wang, Yuzhou ; Rogachev, Victor ; Wolter, Martin ; Gruner, Margit ; Jäger, Anne ; Metz, Peter. / An approach to the bicyclic C-5-C-17/C-19-C-20 (BC) portion of neoclerodane diterpenes by intramolecular Diels-Alder reaction. In: European Journal of Organic Chemistry. 2014 ; Vol. 2014, No. 19. pp. 4083-4088.
    @article{61c3583bea6548bba61475aa73a03f96,
    title = "An approach to the bicyclic C-5-C-17/C-19-C-20 (BC) portion of neoclerodane diterpenes by intramolecular Diels-Alder reaction",
    abstract = "Using a highly diastereoselective intramolecular acrylate [4+2] cycloaddition as the key step, a short route from 3-furaldehyde to a bicyclic building block for the synthesis of neoclerodane diterpenes was developed. A first attempt featuring a conjugate methylation of a dienyl lactone failed, but a streamlined sequence using an all-encompassing intramolecular Diels-Alder reaction of a sterically congested 1,3-diene was successful. A highly diastereoselective intramolecular acrylate [4+2] cycloaddition of a sterically congested 1,3-diene served as the key step in a short synthesis of a BC building block for neoclerodane diterpenes.",
    keywords = "Cross-coupling, Cycloaddition, Michael addition, Natural products, Terpenoids",
    author = "Yuzhou Wang and Victor Rogachev and Martin Wolter and Margit Gruner and Anne J{\"a}ger and Peter Metz",
    year = "2014",
    doi = "10.1002/ejoc.201402165",
    language = "English",
    volume = "2014",
    pages = "4083--4088",
    journal = "Annalen der Pharmacie",
    issn = "0075-4617",
    publisher = "Wiley-VCH Verlag",
    number = "19",

    }

    TY - JOUR

    T1 - An approach to the bicyclic C-5-C-17/C-19-C-20 (BC) portion of neoclerodane diterpenes by intramolecular Diels-Alder reaction

    AU - Wang, Yuzhou

    AU - Rogachev, Victor

    AU - Wolter, Martin

    AU - Gruner, Margit

    AU - Jäger, Anne

    AU - Metz, Peter

    PY - 2014

    Y1 - 2014

    N2 - Using a highly diastereoselective intramolecular acrylate [4+2] cycloaddition as the key step, a short route from 3-furaldehyde to a bicyclic building block for the synthesis of neoclerodane diterpenes was developed. A first attempt featuring a conjugate methylation of a dienyl lactone failed, but a streamlined sequence using an all-encompassing intramolecular Diels-Alder reaction of a sterically congested 1,3-diene was successful. A highly diastereoselective intramolecular acrylate [4+2] cycloaddition of a sterically congested 1,3-diene served as the key step in a short synthesis of a BC building block for neoclerodane diterpenes.

    AB - Using a highly diastereoselective intramolecular acrylate [4+2] cycloaddition as the key step, a short route from 3-furaldehyde to a bicyclic building block for the synthesis of neoclerodane diterpenes was developed. A first attempt featuring a conjugate methylation of a dienyl lactone failed, but a streamlined sequence using an all-encompassing intramolecular Diels-Alder reaction of a sterically congested 1,3-diene was successful. A highly diastereoselective intramolecular acrylate [4+2] cycloaddition of a sterically congested 1,3-diene served as the key step in a short synthesis of a BC building block for neoclerodane diterpenes.

    KW - Cross-coupling

    KW - Cycloaddition

    KW - Michael addition

    KW - Natural products

    KW - Terpenoids

    UR - http://www.scopus.com/inward/record.url?scp=84903315979&partnerID=8YFLogxK

    UR - http://www.scopus.com/inward/citedby.url?scp=84903315979&partnerID=8YFLogxK

    U2 - 10.1002/ejoc.201402165

    DO - 10.1002/ejoc.201402165

    M3 - Article

    AN - SCOPUS:84903315979

    VL - 2014

    SP - 4083

    EP - 4088

    JO - Annalen der Pharmacie

    JF - Annalen der Pharmacie

    SN - 0075-4617

    IS - 19

    ER -