Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (10): 2035-2039.DOI: 10.6023/cjoc201405038 Previous Articles     Next Articles

Articles

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).

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