Constituents of Eupomatia Species. XIII. The Structures of New Lignans From the Tubers and Aerial Parts of Eupomatia bennettii

Abstract

The structures of new extractives from the tubers and aerial parts of Eupomatia bennettii F. Muell. have been assigned as follows: eupomatenoid-15, 2-(4′-methoxyphenyl)-3-methyl-5-(E)-propenylbenzofuran (1); eupomatenoid-16, 7-methoxy-2-(4′-methoxyphenyl)-3-methyl-5-(E)- propenylbenzofuran (3); eupomatenoid-17, 5-allyl-7-methoxy-2-(4′- methoxyphenyl)-3-methylbenzofuran (5); eupomatenoid-18, 5-allyl-2- (3′,4′-dimethoxyphenyl)-7-methoxy-3-methylbenzofuran (6). Eupobennettin was shown to be (2′α,3′α,4̸β,5′α)-5-[3′,4′-dimethyl-5′-(3′,4′,5′-trimethoxyphenyl)tetrahydrofuran-2′-yl]-2,3-dimethoxyphenol (7). Spectroscopic studies and a biomimetic synthesis proved that bennettinone was 2-(4′-allyl-2′-methoxyphenoxy)-1-(3′,4′-dimethoxyphenyl)propan-1-one (10).