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Chin. J. Org. Chem. ›› 2010, Vol. 30 ›› Issue (11): 1705-1710. Previous Articles     Next Articles

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Cedarmycins A和B及其类似物的首次合成

崔庆，王娇，杨海申，谢龙观，徐效华*   

  1. (南开大学元素有机化学研究所 元素有机化学国家重点实验室 天津 300071)
  • 收稿日期:2009-12-24 修回日期:2010-04-11 发布日期:2010-05-18
  • 通讯作者: 崔庆 E-mail:cuiqing@mail.nankai.edu.cn
  • 基金资助:

    基于水稻化感物质设计合成抑制稻田杂草活性分子

First Synthesis of Cedarmycins A and B and Their Analogues

CUI Qing, WANG Jiao, YANG Hai-Shen, XIE Long-Guan, XU Xiao-Hua   

  1. (State Key Laboratory of Elemento-organic Chemistry, Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071)
  • Received:2009-12-24 Revised:2010-04-11 Published:2010-05-18
  • Contact: CUI Qing E-mail:cuiqing@mail.nankai.edu.cn

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The first synthesis of cedarmycins A and B, which were two novel butyrolactone antibiotics isolated from the cultured broth of the actinomycete, was achieved effectively from γ-butyrolactone. The key step was a Barbier reaction of 3-bromomethyl-5H-furan-2-one and formaldehyde to afford the γ-addition product. All structures were confirmed by 1H NMR and 13C NMR spectra. The final compounds were confirmed by 1H NMR, 13C NMR and HRMS techniques, and the results are consistent with the reported natural products.

Key words: natural product, natural antibiotic, Barbier reaction, γ-butyrolacton