Synthetic transformation of hydroxymatairesinol from Norway spruce (Picea abies) to 7-hydroxysecoisolariciresinol, (+)-lariciresinol and (+)-cyclolariciresinol

Patrik Christoffer Eklund, Reijo Sillanpää, Rainer Sjöholm

    Forskningsoutput: TidskriftsbidragArtikelVetenskapligPeer review

    65 Citeringar (Scopus)

    Sammanfattning

    We have developed a method for the transformation of hydroxymatairesinol to optically pure (+)-lariciresinol and (+)-cyclolariciresinol via the hitherto unreported lignan 7-hydroxysecoisolariciresinol. The two naturally occurring isomers of hydroxymatairesinol were reduced with LiAlH4, to a mixture of two epimers or 7-hydroxysecoisolariciresinol, which were further selectively transformed to (+)-lariciresinol and (+)-cyclolariciresinol by an acid catalysed intramolecular cyclisation reaction. The Structure of the major isomer of 7-hydroxysecoisolariciresinol was confirmed by X-ray crystallography and thereby also the absolute configurations of the two isomers of hydroxymatairesinol were unambiguously proven Optical purities were determined by chiral HPLC-MS/MS and optical rotation measurements.
    OriginalspråkOdefinierat/okänt
    Sidor (från-till)1906–1910
    Antal sidor5
    TidskriftJournal of the Chemical Society, Perkin Transactions 1
    Utgåva16
    DOI
    StatusPublicerad - 2002
    MoE-publikationstypA1 Tidskriftsartikel-refererad

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