Verbenachalcone的另法全合成

Modified Total Synthesis of Verbenachalcone

用一种新的简便方法对Verbenachalcone进行全合成,针对目标物的结构特征,将其切为2个合成片段,即化合物4和6,然后再将2个片段连接.从对羟基苯甲醛(2)开始经过溴代、乙酰化、Ullmann反应、甲氧甲基化、羟醛缩合、脱保护和催化加氢等7步反应完成了标题化合物的全合成,总收率为39.1%,合成的关键步骤是3-溴-4-羟基苯甲醛(3)和香兰素进行的Ullmann反应.关键中间体与最终产物的化学结构经1HNMR,13CNMR和ESI-MS等表征确认.

A new and simple method for synthesis of verbenachalcone（ 1） was reported. A method for reverse synthesis design was adopted to two synthetic fragments,compound 4 and compound 6. Then the two fragments were combined together,starting from p-hydroxybenzaldehyde（ 2） through acetylation,bromination, Ullmann reaction,methoxymethylation,aldol condensation,deprotection,catalytic hydrogenation seven steps to target compound,with total yield of 39. 1% . The key steps were the Ullmann reaction of 3-bromo-4hydroxybenzaldehyde（ 3） with vanilline. The chemical structures of the key intermediate and final target product were verified by 1H NMR,13C NMR and ESI-MS.