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Synthesis of R-(-)-imperanene from the natural lignan hydroxymatairesinol
Patrik C Eklund1, Annika I Riska, Rainer E Sjöholm
1Department of Organic Chemistry, Process Chemistry Group, Abo Akademi University, Piispankatu 8, FIN-20500 Turku, Finland. paeklund@abo.fi
Abstract:
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%).