22 2,3-dibenzylbutyrolactone lignansの絶対構造について

概要

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The chemical assignments were given to the absolute configurations of 2-(3,4,5-trimethoxybenzyl)-3-(3,4-methylenedioxybenzyl) butyrolactone(4), thujaplicatin trimethyl ether(10), pluviatolide (2), 2-(3,4-dimethoxybenzyl)-3-(3,4-methylenedioxybenzyl)butyrolactone(3) [2R,3R], methyltrachelogenin(20), hydroxythujaplicatin trimethyl ether(23) [2S,3S], thujastandin dimethyl ether(24), dihydroxythujaplicatin trimethyl ether(25) [2S,3R] and hydroxymatairesinol dimethyl ether(35)[2R,3R,5R], allo-hydroxymatairesinol dimethyl ether(38) [2R,3R,5S] by their conversion to known compounds, whose absolute configurations have already been established. From considerations of the configuration at C-2,3 position of butyrolactone ring on the basis of CMR and CD spectral data (Table 2 and 3) of lignans listed in Table 1, it was demonstrated that CMR is highly useful for elucidation of the relative configuration and then CD for assignment of the absolute configuration.
天然有機化合物討論会の論文
1978-08-22