莽草酸中间体-3,4-异亚丙基莽草酸内酯的合成

Synthesis of Shikimic Acid Intermediates-3,4-isopropylidene Shikimic Acid Lactone

以D-(-)-奎尼酸为原料,丙酮为保护剂,将顺式邻二羟基转化成缩酮得到3,4-异亚丙基奎尼酸内酯,再将3,4-异亚丙基奎尼酸内酯1位羟基区域选择性脱水得到3,4-异亚丙基莽草酸内酯。探讨了不同保护剂,催化剂、反应时间对缩酮收率的影响。优化工艺条件为:丙酮为保护剂,对甲苯磺酸作催化剂,反应时间为4 h。2步反应总收率为33%。

3,4-Isopropylidene shikimic acid lactone was synthesized using D-（-）-quinic acid as the starting material via ketol reaction followed by selective dehydration of 1-hydroxyl Groups. Effects of different protective agents on adjacent hydroxyl groups, catalysts and reaction time on the ketol reaction were investigated. The results showed that the optimum parameters were as following： acetone as protective agent, p-toluene sulfonic acid as catalyst, reaction time of 4 h were. The total yield was of 33%.