多氧取代1-环己烯甲醇的合成  

Novel method for synthesis of polyoxygenated 1-cyclohexene-1yl-methanol

作　　者：李振卿[1] 许琼明[1] 敖桂珍[1] 袁志军[1] 

机构地区：[1]苏州大学药学院,江苏苏州215123

出　　处：《化学试剂》2009年第6期469-470,472,共3页Chemical Reagents

摘　　要：以莽草酸为原料,与甲醇成酯,然后丙酮叉保护顺式的邻二羟基,叔丁基二甲硅氯保护另一个羟基,最后用氢化铝锂和三氯化铝还原,得到标题化合物,其结构经IR1、HNMR、HR-MS确证,总产率86.5%。对还原反应的条件进行了探索,其收率高达95.2%。A novel method was developed and carefully studied for the synthesis of polyoxygenated cyclohexene-yl-methanol from shikimic acid by means of esterification with methanol, followed by protection by DMP and TBDMSC1 and reduction by mixed THF solution of lithium aluminum hydride and aluminum chloride. The structure of the final product was identified by ^1H NMR, IR and MS methods, and the total product yield could reach 86.5 %. Under optimized condition the yield of product obtained via the improved reduction step could reach 95.2%.

关 键 词：多氧取代1-环己烯甲醇 Α Β-不饱和酯 氢化铝锂 三氯化铝 还原 

分 类 号：O623.412[理学—有机化学]