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化学学报
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化学学报 ›› 2008, Vol. 66 ›› Issue (17): 1991-1994. 上一篇    下一篇

研究论文

关于茎点霉联烯酸丙的绝对构型

简亚军 张 艳 伍贻康*

  

  1. (中国科学院上海有机化学研究所 生命有机化学国家重点实验室 上海 200032)

  • 投稿日期:2008-02-25 修回日期:2008-04-28 发布日期:2008-09-14
  • 通讯作者: 伍贻康

On the Absolute Configuration of Phomallenic Acid C

JIAN, Ya-Jun ZHANG, Yan WU, Yi-Kang*   

  1. (State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry,
    Chinese Academy of Sciences, Shanghai 200032)
  • Received:2008-02-25 Revised:2008-04-28 Published:2008-09-14
  • Contact: WU, Yi-Kang

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茎点霉联烯酸丙1是一具全新作用机制的天然抗菌化合物, 其绝对构型在全合成中是从关键中间体炔丙醇4的绝对构型来推定的. 由于后者本身依赖于经验规则, 进一步获取实验证据显得很有必要. 为此我们用Mosher酯法对炔丙醇4的绝对构型进行了测定. 结果表明原先推定的绝对构型是正确的.

关键词: Mosher酯, 对映体, 丙炔醇, 不对称还原, 联烯

The absolute configuration of phomallenic acid C (1), a recently isolated natural antibiotic with a novel mode of action, was previously established in a total synthesis through deduction from the configuration of a key intermediate 4 assigned on an empirical basis. Further experimental evidence is therefore highly desirable. In the present work the absolute configuration of the key propargylic alcohol 4 was determined using the method developed by Mosher. The results show that the previously assigned absolute configuration of 1 is correct.

Key words: Mosher ester, enantiomer, propargylic alcohol, asymmetric reduction, allene