Abstract
Several homoisoflavonoidal compounds, namely the monomethyl ethers ((IIIb) and (IVb)) of methylophiopogonones A and B, isoophiopogonone A monomethyl ether (VIIIb) and desmethylisoophiopogonone B (IXa), which were derived from the constituents of Ophiopogonis tuber (tuber of Ophiopogon japonicus KER-GAWLER var. genuinus MAXIM., Liliaceae), have been synthesized. The chemical and spectroscopical assignments reported in the previous papers have been confirmed by the synthesis of methylophiopogonone A (IIIa ; 5, 7-dihydroxy-6, 8-dimethyl-3-(3, 4-methylenedioxybenzyl)-chromone), methylophiopogonone B (IVa ; 5, 7-dihydroxy-3-(4-methoxybenzyl)-6, 8-dimethyl-chromone), isoophiopogonone A (VIIIa ; 5, 7-dihydroxy-8-methyl-3-(3, 4-methylenedioxybenzyl)-chromone) and desmethylisoophiopogonone B (IXa ; 5, 7-dihydroxy-3-(4-hydroxybenzyl)-8-methylchromone).