从(-)-莽草酸出发合成(3R,5R)-3,4,5-三苯甲酰氧基环己酮  

Syntheses of(3R,5R)-3,4,5-Triphenyloxycyclohexanone Starting from(-)-Shikimic Acid

作　　者：朱星亮 罗永强 刘世领 施小新 ZHU Xing-liang;LUO Yong-qiang;LIU Shi-ling;SHI Xiao-xin(Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China;Qingping Pharmaceutical Co., Ltd., Shanghai 2017101, China)

机构地区：[1]华东理工大学药学院上海市化学生物学重点实验室,上海200237 [2]青平药业有限公司,上海201710

出　　处：《合成化学》2021年第6期508-514,共7页Chinese Journal of Synthetic Chemistry

基　　金：国家自然科学基金资助项目(20972048)。

摘　　要：报道了一种合成手性中间体(3R,5R)-3,4,5-三羟基环己酮的新方法。首次以(-)-莽草酸为起始原料,经苯甲酰化、双键氢化、选择性还原甲酯、羟基碘代、碘代烃消除、双键双羟化、片哪醇断裂等步骤,以44.9%的总收率合成了(3R,5R)-3,4,5-三苯甲酰氧基环己酮,所有化合物的结构经^(1)H NMR、^(13)C NMR、IR及MS等确证。In this paper,a novel synthesis of(3R,5R)-3,4,5-trihydroxycyclohexanone from(-)-shikimic acid was studied.For the first time,(3R,5R)-3,4,5-triphenyloxycyclohexanone was synthesized from(-)-shikimic acid in 44.9%overall yield via benzoylation,hydrogenation of double bond,selective reduction of methyl ester,substitution of hydroxyl with iodine,elimination of iodide,dihydroxylation of double bond and cleavage of pinacol.The structures of all compounds were characterized by ^(1)H NMR,^(13)C NMR,IR and MS.

关 键 词：环己酮 莽草酸 苯甲酰化 选择性还原 手性中间体 合成 

分 类 号：TQ630[化学工程—精细化工] O62[理学—有机化学]