天然产物紫檀茋及(E)-3,5,3′-三甲氧基-4′-羟基二苯乙烯的合成

Synthesis of Natural Products Pterostilbene and E-3,5,3′-Trimethoxy-4′-Hydroxystilbene

以3,5-二羟基苯乙酮为起始原料,经甲基化反应、Willgerodt-Kindler重排得到3,5-二甲氧基苯乙酸(4),化合物4分别与对羟基苯甲醛以及香兰素发生Perkin缩合反应得到E-2,3-二芳基丙烯酸(7a,7b)。化合物7a,7b分别经脱羧-异构化反应得到天然产物紫檀茋(8a)及(E)-3,5,3′-三甲氧基-4′-羟基二苯乙烯(8b),总收率分别为48.7%和43.8%。其化学结构经IR、EI-MS、1HNMR确证。

The synthesis of two natural products pterostilbene（8a） and its 3′-methoxylated derivative（E-3,5,3′-trimethoxy-4′-hydroxystilbene,8b） were described.Starting from 3,5-dihydroxyacetophenone,3,5-dimethoxylphenyl acetic acid（4） was prepared by methylation and Willgerodt-Kindler rearrangement.Perkin condensation between compound 4 and p-hydroxybenzaldehyde or vanillin afforded 7a and 7b,which transformed by decarboxylation/isomerization process gave pterostilbene（8a） and E-3,5,3′-trimethoxy-4′-hydroxystilbene（8b） in overall yield of 48.7% and 43.8%,respectively.The structure of title compounds were confirmed by IR,EI-MS,and 1H NMR spectral data.