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2014 , Vol. 34 >Issue 10: 2035 - 2039

DOI: https://doi.org/10.6023/cjoc201405038

研究论文

格尔德霉素C(11)～C(21)片段的合成

  • 李永强 ,
  • 严睿 ,
  • 卞传才 ,
  • 张智 ,
  • 刘迪 ,
  • 俞晓明
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  • 天然药物活性物质与功能国家重点实验室 中国医学科学院药物研究所 北京 100050

收稿日期: 2014-05-29

  修回日期: 2014-06-05

  网络出版日期: 2014-06-16

基金资助

国家自然科学基金（No. 21272279）资助项目.

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Practical Synthesis of the C(11)～C(21) Fragment of Geldanamycin

  • Li Yongqiang ,
  • Yan Rui ,
  • Bian Chuancai ,
  • Zhang Zhi ,
  • Liu Di ,
  • Yu Xiaoming
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  • State Key Laboratory of Bioactive Substance and Function of Natural Medicine, Institute of Materia Medica, Peking Union Medical College & Chinese Academy of Medical Sciences, Beijing 100050

Received date: 2014-05-29

  Revised date: 2014-06-05

  Online published: 2014-06-16

Supported by

Project supported by the National Natural Science Foundation of China (No. 21272279).

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摘要

以D-三乙酰葡萄糖烯为最初原料，经三步反应合成了已知内酯化合物5. 以羰基α位亚甲基化、底物诱导的不对称催化氢化反应为关键步骤，构建了关键的C（14）位手性中心. 最终，经10步反应、以24%的总产率合成了苯醌安莎霉素类天然产物格尔德霉素（Geldanamycin）的C（11）～C（21）片段.

关键词： 格尔德霉素; 手性γ-丁内酯; 不对称合成

本文引用格式

李永强 , 严睿 , 卞传才 , 张智 , 刘迪 , 俞晓明 . 格尔德霉素C(11)～C(21)片段的合成[J]. 有机化学, 2014 , 34(10) : 2035 -2039 . DOI: 10.6023/cjoc201405038

Abstract

The C(11)～C(21) fragment of benzoquinone ansamycin geldanamycin was synthesized in 10 steps and 24% overall yield from known lactone 5, which was prepared from tri-O-acetyl-D-glucal in 3 steps. The key steps included an α-methylenation of lactone 5, followed by a substance induced facial selective hydrogenation.

Key words： geldanamycin; chiral γ-lactone; asymmetric synthesis

参考文献

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