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

    Keywords

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

    ASJC Scopus subject areas

    • Organic Chemistry
    • Physical and Theoretical Chemistry

    Fingerprint Dive into the research topics of 'An approach to the bicyclic C-5-C-17/C-19-C-20 (BC) portion of neoclerodane diterpenes by intramolecular Diels-Alder reaction'. Together they form a unique fingerprint.

  • Cite this