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

A1 Originalartikel i en vetenskaplig tidskrift (referentgranskad)


Interna författare/redaktörer


Publikationens författare: Patrik Eklund, Reijo Sillanpää, Rainer Sjöholm
Förläggare: ROYAL SOC CHEMISTRY
Publiceringsår: 2002
Tidskrift: Journal of the Chemical Society, Perkin Transactions 1
Tidskriftsakronym: J CHEM SOC PERK T 1
Nummer: 16
Artikelns första sida, sidnummer: 1906
Artikelns sista sida, sidnummer: 1910
Antal sidor: 5
ISSN: 1472-7781


Abstrakt

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.

Senast uppdaterad 2019-17-10 vid 01:07