三种O-异戊烯基苯丙素类天然产物的首次合成  

First Synthesis of Three Naturally Occurring O-Prenylated Phenylpropanoids

作　　者：王倩[1] 何侃侃[1] 侯自杰[1] 

机构地区：[1]兰州大学有机化学研究所应用有机化学国家重点实验室,兰州730000

出　　处：《有机化学》2003年第2期182-186,共5页Chinese Journal of Organic Chemistry

摘　　要：以香草醛为起始原料 ,经O 异戊烯基化、Wittig反应、水解、还原、氧化等反应步骤 ,首次合成了三种苯丙素类天然产物boropinolA (1) ,boropinalC (2 ) ,boropinicacid (3) .所有化合物结构均由核磁共振氢谱、质谱及红外光谱确证 .用X射线衍射法测定了The first synthesis of three naturally occurring phenylpropanoids, boropinol A (1), boropinal C (2) and boropinic acid (3), is described. The reaction of vaniline (4) with prenyl bromide in DMF gave the O-prenylated product 5 in 84% yield. Condensation of 5 with Ph3P = CHCO2Et in DME produced ester 6 in 52% yield. Hydrolysis of 6 with aqueous KOH followed by acidification gave boropinic acid (3) in 91 % yield. Compound 3 was obtained as a nice crystal instead of a liquid as that reported in literature. The structure of 3 was confirmed by X-ray crystal structural analysis in addition to its solution spectrum data. Reduction of 3 by LiAlH4 in dry diethyl ether gave a mixture of compound 1 and 7. This mixture was not seperated and was oxidized by K2Cr2O7 in DMSO to give compound 2 in 61% yield. Pure boropinol A (1) was obtained in 70% yield by the reduction of 2 with NaBH4 in CH3OH.

关 键 词：O-异戊烯基苯丙素 天然产物 boropinalA boropinalC boropinicAcid 合成 晶体结构 

分 类 号：O629[理学—有机化学] R284.3[理学—化学]