高等学校化学学报 ›› 2005, Vol. 26 ›› Issue (2): 264.

• 研究简报 • 上一篇    下一篇

对映体纯1-甲基-7-氧杂双环[2.2.1]庚烷-2-酮的制备

关玉昆, 房丽晶, 郑国君, 李裕林   

  1. 兰州大学功能有机分子化学国家重点实验室, 有机化学研究所, 兰州 730000
  • 收稿日期:2003-12-01 出版日期:2005-02-10 发布日期:2005-02-10
  • 通讯作者: 李裕林(1935年出生),男,教授,博士生导师,从事有机合成化学研究.E-mail:liyl@lzu.edu.cn E-mail:liyl@lzu.edu.cn
  • 基金资助:

    国家自然科学基金(批准号:20272021)资助

Preparation of Enantiomerically Pure 1-Methyl-7-oxabicyclo[2.2.1]heptan-2-one

GUAN Yu-Kun, FANG Li-Jing, ZHENG Guo-Jun, LI Yu-Lin   

  1. State Key Laboratory of Applied Organic Chemistry, Institute of Organic Chemistry, Lanzhou University, Lanzhou 730000, China
  • Received:2003-12-01 Online:2005-02-10 Published:2005-02-10

关键词: 1-甲基-7-氧杂双环[2.2.1]庚烷-2-酮, 萜类化合物, 扁桃酸, 拆分

Abstract: (±)-1-Methyl-7-oxabicyclo[2.2.1]heptan-2-one (1) is a versatile chiral building block for terpenoids. It could be applied in total synthesis of eudesmanes, agarofurans and norcarotenoids. Compound (±)-1 was reduced to alcohol (±)-2. Compound (±)-2 was esterified with commercial available optically pure (S)-(+)-mandelic acid. The diastereomeric ester mixture was separated with preparative HPLC method. After oxidation of the saponified products of diastereomeric ester (+)-4 and (+)-5 respectively, both optically pure enantiomers of compound 1 were prepared for the first time in four steps with an overall yield of 70%. The absolute configurations of (+)-1 and (-)-1 were determined as (+)-(1R,4S)-1-methyl-7-oxabicyclo[2.2.1] heptan-2-one and (-)-(1S,4R)-1-methyl-7-oxabicyclo[2.2.1] heptan-2-one.

Key words: 1-Methyl-7-oxabicyclo[2.2.1]heptan-2-one, Terpenoids, Mandelic acid, Resolution

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