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

Patrik Christoffer Eklund, Reijo Sillanpää, Rainer Sjöholm

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    Abstract

    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.
    Original languageUndefined/Unknown
    Pages (from-to)1906–1910
    Number of pages5
    JournalJournal of the Chemical Society, Perkin Transactions 1
    Issue number16
    DOIs
    Publication statusPublished - 2002
    MoE publication typeA1 Journal article-refereed

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