番茄红素的全合成

Total Synthesis of Lycopene

开发了一条番茄红素的全合成工艺,以香叶醇为原料,经氧化得到柠檬醛,柠檬醛和C4-膦酸酯经Wittig-Horner缩合得到C14-烯醇醚,再经水解得到C14-醛,C14-醛与偕二膦酸酯缩合得到C15-膦酸酯,C15-膦酸酯经双键移位与C10-双醛缩合得到番茄红素粗品。以乙醇为溶剂回流搅拌可将粗品中反式体的含量提高至98%以上,反应总收率为23.5%。

In this study,a total synthesis process of lycopene was developed.Citral was obtained from geraniol by oxidation.Citral and C4-phosphonate were condensed by Wittig-Horner to C14-enol ether,and then C14-enol ether was hydrolyzed to C14-aldehyde.C14-aldehyde was condensed with methylenebisphosphonic acid tetraethyl ester to obtain C15-phosphonate,and C15-phosphonate was condensed with C10-dialdehyde to obtain crude lycopene.Reflux stirring with ethanol can increase the content of trans-isomer in the crude product to more than 98%,and the total yield of the reaction is 23.5%.