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

    Результат исследований: Материалы для журналаСтатьярецензирование

    6 Цитирования (Scopus)

    Аннотация

    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.

    Язык оригиналаАнглийский
    Страницы (с-по)4083-4088
    Число страниц6
    ЖурналEuropean Journal of Organic Chemistry
    Том2014
    Номер выпуска19
    DOI
    СостояниеОпубликовано - 2014

    ASJC Scopus subject areas

    • Organic Chemistry
    • Physical and Theoretical Chemistry

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