Synthesis of (-)-Matairesinol, (-)-Enterolactone, and (-)-Enterodiol from the Natural Lignan Hydroxymatairesinol

Patrik Christoffer Eklund, Anna Lindholm, Jyri-Pekka Mikkola, Annika Smeds, Reko Lehtilä, Rainer Sjöholm

    Forskningsoutput: TidskriftsbidragArtikelVetenskapligPeer review

    54 Citeringar (Scopus)

    Sammanfattning

    We describe here a four-step semisynthetic method for the preparation of enantiomerically pure (-)-enterolactone starting from the readily available lignan hydroxymatairesinol from Norway spruce (Picea abies). Hydroxymatairesinol was first hydrogenated to matairesinol. Matairesinol was esterified to afford the matairesinyl 4,4'-bistriflate, which was deoxygenated by palladium-catalyzed reduction to 3,3'-dimethylenterolactone. Demethylation of 3,3'-dimethylenterolactone and reduction with LiAlH4 yielded (-)-enterolactone and (-)-enterodiol, respectively.
    OriginalspråkOdefinierat/okänt
    Sidor (från-till)491–493
    Antal sidor3
    TidskriftOrganic Letters
    Volym5
    Utgåva4
    DOI
    StatusPublicerad - 2003
    MoE-publikationstypA1 Tidskriftsartikel-refererad

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