Synthesis of (-)-Sugiresinol Dimethyl Ether Utilizing (-)-Quinic Acid

Sugiresinol dimethyl ether, a derivative of (-)-sugiresinol isolated from Cryptomeria japonica, was synthesized through 1,4-conjugate addition of arylmetal reagent to a substituted chiral 2-cyclohexen-1-one derived from (-)quinic acid.(-)-Sugiresinol (1a) is a norlignan isolated from heartwood of Cryptomeria japonica by Funaoka et al. 1 in 1963, and its chemical structure including absolute stereochemistry was determined by Enzell et al. 2 in 1967.(-)-Sugiresinol (1a) has been reported to show biological activities such as antifungal activity, 3 inhibitory effect on cyclic AMP phosphodiesterase, 4 inhibitory activity against C. shiitake hyphae growth and fruiting body formation, 5 and vinyl polymerization-inhibitory activity. 6