Synthesis of R-(-)-imperanene from the natural lignan hydroxymatairesinol.
A convenient and high yielding method for the synthesis of R-(-)-imperanene, starting from the readily available natural lignan hydroxymatairesinol from Norway spruce, was developed. Hydroxymatairesinol was degraded in strongly basic aqueous conditions to (E)-4-(4-hydroxy-3-methoxyphenyl)-2-(4-hydroxy-3-methoxyphenylmethyl)but-3-enoic acid, which was esterified and then reduced by LiAlH(4) to afford R-(-)-imperanene. The configuration at the crucial stereocenter was preserved in the synthesis, and the obtained product was identified by optical rotation measurements and chiral HPLC analyses as the R-(-)-enantiomer (ee 86-92%).
Eklund
Patrik C
PC
Department of Organic Chemistry, Process Chemistry Group, Abo Akademi University, Piispankatu 8, FIN-20500 Turku, Finland. paeklund@abo.fi
Riska
Annika I
AI
Sjöholm
Rainer E
RE
D007202:Indicators and Reagents; D017705:Lignans / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D010636:Phenols / Q000138:chemical synthesis* / Q000737:chemistry*; D028222:Picea / Q000737:chemistry*
D007202:Indicators and Reagents; D017705:Lignans; D010636:Phenols; C419306:hydroxymatairesinol; C093767:imperanene