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

A1 Journal article (refereed)

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Publication Details

List of Authors: Patrik Eklund, Reijo Sillanpää, Rainer Sjöholm
Publication year: 2002
Journal: Journal of the Chemical Society, Perkin Transactions 1
Journal acronym: J CHEM SOC PERK T 1
Issue number: 16
Start page: 1906
End page: 1910
Number of pages: 5
ISSN: 1472-7781


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.

Last updated on 2020-18-02 at 04:43