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有机化学
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有机化学 ›› 2010, Vol. 30 ›› Issue (11): 1705-1710. 上一篇    下一篇

研究论文

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

PDF

1259

被引次数

7 | 5

Cedarmycins A和B是近年从放线菌的次生代谢物中分离得到的一种新型的天然抗生素, 本文以γ-丁内酯为原料首次合成了该类化合物. 其关键步骤为3-溴甲基-5H-呋喃-2-酮与甲醛发生的γ位迁移的Barbier反应. 各中间体都通过1H NMR和13C NMR得到证实. 最终产品通过1H NMR, 13C NMR和HRMS证实与文献所报道相一致.

关键词: 天然化合物, 天然抗生素, Barbier反应, γ-丁内酯

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