有机化学 ›› 2014, Vol. 34 ›› Issue (10): 2035-2039.DOI: 10.6023/cjoc201405038 上一篇    下一篇

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   

  1. 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 发布日期:2014-06-16
  • 通讯作者: 俞晓明 E-mail:mingxyu@imm.ac.cn
  • 基金资助:

    国家自然科学基金(No. 21272279)资助项目.

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

Li Yongqiang, Yan Rui, Bian Chuancai, Zhang Zhi, Liu Di, Yu Xiaoming   

  1. 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:2014-05-29 Revised:2014-06-05 Published:2014-06-16
  • Supported by:

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

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

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