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

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    Abstract

    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.
    Original languageUndefined/Unknown
    Pages (from-to)491–493
    Number of pages3
    JournalOrganic Letters
    Volume5
    Issue number4
    DOIs
    Publication statusPublished - 2003
    MoE publication typeA1 Journal article-refereed

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