番茄红素的全合成

Total synthesis of lycopene

设计完成了一条新的全反式番茄红素全合成路线:由4,8-二甲基-3,7-壬二烯-1-醛(2)与丙醛(3)经Aldol缩合反应制备关键中间体2,6,10-三甲基-2,5,9-十一烷三烯-1-醛(4),再与偕二膦酸酯(5)经Wittig-Horner反应得到3,7,11-三甲基-1,3,6,10-四烯十二烷基膦酸二乙酯(6),最后与十碳双醛(7)反应得到全反式番茄红素(1),总收率为58.7%。与以往的全合成路线相比,具有步骤少、工艺简单、反应收率高等特点,具有较大的工业化生产潜力。

A novel route to the total synthesis of lycopene was described. The synthesis was based on the following three steps： （i）the aldol condensation between 4, 8-dimethylnona-3, 7-dienal（2）and propionaldehyde（3）led to the key intermediate, 2, 6, 10-trimethylundeca-2, 5, 9-trienal（4）; （ii）3, 7, 11-trimethyldodeca-1, 3, 6, 10-tetraenylphosphonate（6）could be prepared via the modified Wittig-Horner reaction between（4） and methylenebisphosphonic acid tetraethyl ester（5）; （iii）another modified Wittig-Horner reaction between（6）and C10-triene dialdehyde（7）could produce all-E-lycopene（1）. The overall yield was 58. 7%. This approach offers many advantages including less steps, simple operations, high-yielding compared with the conventional synthetic routes, and exhibits a potential for large-scale production.