高等学校化学学报 ›› 2001, Vol. 22 ›› Issue (4): 584.

• 研究论文 • 上一篇    下一篇

手性3,7-二甲基-5,6-二羟基-辛-7-烯醛中间体的合成

贾彦兴, 吴滨, 涂永强   

  1. 兰州大学化学系应用有机化学国家重点实验室, 兰州 730000
  • 收稿日期:2000-03-06 出版日期:2001-04-24 发布日期:2001-04-24
  • 通讯作者: 涂永强(1958年出生),男,博士,教授,博士生导师,主要从事生物有机化学研究.E-mail:tuyq@lzu.edu.cn E-mail:tuyq@lzu.edu.cn
  • 基金资助:

    教育部博士学科点基金(批准号:96073006);教育部跨世纪人才基金;国家杰出青年基金(批准号:29925205)资助

Synthesis of Chiral Intermediate (3S,5S,6S)-3,7-Dimethyl-5,6-dihydroxy-7-en-octanal of Didemnaketals Analogue

JIA Yan-Xing, WU Bin, TU Yong-Qiang   

  1. Department of Chemistry, National Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China
  • Received:2000-03-06 Online:2001-04-24 Published:2001-04-24

摘要: 以天然长叶薄荷酮[R-(+)-Pulegone]为起始原料,经过一系列立体选择性化学反应步骤,成功地建立了3个手性中心,从而完成了具有抗艾滋病活性Didemnaketals类似物的关键中间体3,7-二甲基-5,6-二羟基-辛-7-烯醛中间体的合成.发现PCC与三级环氧醇8和9的非对映选择性反应,使得9被完全氧化,而8以93%的产率回收,其de值高达98%.

关键词: 螺环缩酮, R-(+)-Pulegone, 非对映选择性氧化, 3, 7-二甲基-5, 6-二羟基-辛-7-烯醛中间体

Abstract: Astereoselective synthesis of (3 S,5S,6S )-3,7-dimethyl-5,6-dihydroxy-7-en-octanal, a key intermediate, for the synthesis of the HIVinhibitory didemnaketals analogue, was performed via a series of reactions from the natural(+)-pulegone. In this approach, an interesting and valuable diastereo recognizable reaction between tertiary hydroxyepoxides and PCCwas found. Therefore, the mixture of compounds 8 and 9 was treated with PCCto recover 8 in 93% yield and de 98% purity.

Key words: Spiroketal, R-(+)-Pulegone, Diastereo-recognizable oxidation reaction, 3,7-Dimethyl-5,6-dihydroxy-7-en-octanal intermediate

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