高等学校化学学报

高等学校化学学报 ›› 2004, Vol. 25 ›› Issue (6): 1069.

• 研究论文 • 上一篇    下一篇

光学纯反式-(+)-水合蒎醇的新方法合成

汪秋安, 罗俊霞, 廖头根   

  1. 湖南大学化学化工学院, 化学生物传感与计量学国家重点实验室, 长沙 410082
  • 收稿日期:2003-04-25 出版日期:2004-06-24 发布日期:2004-06-24
  • 通讯作者: 汪秋安(1962年出生),男,博士,副教授,从事天然产物化学和有机合成研究.E-mail:wangqiuan@yahoo.com E-mail:wangqiuan@yahoo.com
  • 基金资助:

    教育部留学回国人员科研启动基金(批准号:教外司留[2002]247号)资助

A Novel Synthesis of Optically Pure trans-(+)-Sobrerol

WANG Qiu-An, LUO Jun-Xia, LIAO Tou-Gen   

  1. College of Chemistry and Chemical Engineering, State Key Laboratory of Chemo/Biosensing and Chemometrics, Hunan University, Changsha 410082, China
  • Received:2003-04-25 Online:2004-06-24 Published:2004-06-24

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被引次数

13

摘要： 以3,5-二羟基-4-甲基苯甲酸甲酯为原料,通过7步反应,高产率地合成了反式-(+)-水合蒎醇[(+)-1],其结构通过IR,MS和NMR等技术进行了确认,该化合物的光学纯度e.e.高达99%.

关键词: 反式-(+)-水合蒎醇, 萜二醇, 光学纯度

Abstract: A novel and highly efficient synthesis of optically pure trans-(+)-sobrerol,starting from methyl 3,5-dihydroxy-4-methyl benzoate(2) in 7 steps with overall yield 27%,was reported. The key intermediate(+)-5 was prepared in remarkably high yield by lipase__catalyzed asymmetrization of 4. A critical step to stereoselectively inverse the configuration of(+)-6 was realized under Mistunobu conditions. The structures of all the compounds were confirmed by IR,MS and NMR spectra.

Key words: trans-(+)-Sobrerol, Terpinediol, Optical purity

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