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报道了一条合成天然产物3,4-二香草基四氢呋喃阿魏酸酯的方法.以香草醛为原料,经过两步Stobbe反应构建木脂素骨架,然后再加氢、LiAlH4还原,产物经柱层析分离后得到两个异构体meso-和threo-(±)-开环落叶松脂素;它们分别与TsCl作用,发生分子内反应得到关键的四氢呋喃木脂素中间体meso-和threo-(±)-shonanin;最后,分别与MOM保护的阿魏酸缩合得到倍半木脂素threo-(±)-3,4-二香草基四氢呋喃阿魏酸酯和衍生物erythro-(±)-3,4-二香草基四氢呋喃阿魏酸酯.合成采用汇聚法,经13步,以约8%~9%的总产率得到了目标产物.
Reported a method for the synthesis of natural product 3,4-di-vanillyltetrahydrofuran ferulic acid ester.With vanillin as raw material, two-step Stobbe reaction was used to construct lignan skeleton, and then hydrogenation, LiAlH4 reduction, the product through the column After separation, two isomers, meso- and threo- (±) - ring-opening laendolipid, were obtained; they reacted with TsCl, respectively, to produce the intramolecular reaction of meso- and threo- (±) ) -shonanin. Finally, the sesquatillo-threo- (±) -3,4-dioxan-based tetrahydrofurane ferulic acid ester and the derivative erythro- (±) -3 were obtained by condensation with MOM- Di-vanillyltetrahydrofuran ferulic acid ester was synthesized using the convergent method, the target product was obtained in 13 steps with a total yield of about 8% ~ 9%.