6533b83afe1ef96bd12a7a61
RESEARCH PRODUCT
Synthetic transformation of hydroxymatairesinol from Norway spruce (Picea abies) to 7-hydroxysecoisolariciresinol, (+)-lariciresinol and (+)-cyclolariciresinol
Rainer SjoeholmPatrik EklundReijo Sillanpaeaesubject
LariciresinolLignanbiologyPicea abiesGeneral Medicinebiology.organism_classificationTransformation (genetics)chemistry.chemical_compoundHydroxymatairesinolchemistryIntramolecular forceBotanyOrganic chemistryEpimerOptical rotationdescription
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 of 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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2003-01-14 | J. Chem. Soc., Perkin Trans. 1 |