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.
|Number of pages||5|
|Journal||Journal of the Chemical Society, Perkin Transactions 1|
|Publication status||Published - 2002|
|MoE publication type||A1 Journal article-refereed|