天然产物(E)-白黎芦醇的全合成

Total synthesis of natural product (E)-resveratrol

从价廉易得的 3,5 二羟基苯甲酸为原料 ,通过甲基化、肼化、氧化反应得到中间体 3,5 二甲氧基苯甲醛 ,与对甲氧基苄磷酸酯经Witting Horner缩合反应得到单一反式的 3,4′ ,5 三甲氧基芪 ,最后用BBr3 /CH2 Cl2 脱去甲基保护基 ,合成目标产物 (E) 白黎芦醇 ,总收率为 35 7%。

The total synthesis of the biological activite substance ( trans ) resveratrol (5) was described with a good overall yield(35 7%).Starting from 3,5 dihydroxy benzoic acid,methyl 3,5 dimethoxybenzonate was prepared in 92 9% yield.The reaction of the ester with hydrazine hydrate followed by oxidation with K 3 gave the key intermediate 3,5 dimethoxybenzaldehyde,which was condensed with diethyl ( p methoxy benzyl) phosphonate to give only trans isomer 3,4′,5 trimethylstilbene in 60 7% yield.The synthesis of (trans ) resveratrol was completed by the deprotection reaction with BBr 3/CH 2Cl 2.