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有机化学
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有机化学 ›› 2010, Vol. 30 ›› Issue (07): 1017-1020. 上一篇    下一篇

研究论文

青霉烯和碳青霉烯类抗生素关键中间体4-乙酰氧基氮杂环丁酮的立体选择性合成

徐晓波123，杨迎宾1，邓琴1，向莉1，向建南*123   

  1. (1湖南大学化学化工学院 长沙 410082)
    (2湖南大学生物医学工程中心 长沙 410082)
    (3湖南大学化学生物传感与化学计量学国家重点实验室 长沙 410082)
  • 收稿日期:2009-06-29 修回日期:2009-09-21 发布日期:2010-02-10
  • 通讯作者: 向建南 E-mail:jnxiang@hnu.cn
  • 基金资助:

    湖南省科技厅（NO.K09028）湖南省长沙市科技局（NO.K0802152-31）

Stereoselective Synthesis of 4-Acetoxyazetidione: the Key Intermediate of Penem and Carbapenem Antibiotics

Xu Xiaobo123 Yang Yingbin1 Deng Qin1 Xiang Li1 Xiang Jiannan*123   

  1. (1College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082) (2Biomedical Engineering Center, Hunan University, Changsha 410082) (3State Key Laboratory of Chemo/Biosensing and Chemometrics, Hunan University, Changsha 410082)
  • Received:2009-06-29 Revised:2009-09-21 Published:2010-02-10
  • Contact: XIANG Jian-Nan E-mail:jnxiang@hnu.cn

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被引次数

1

以6,6-二溴青霉烷酸甲酯为原料经过氧化、格氏反应、还原、羟基保护、开环、甲基化、脱保护和乙酰化合成青霉烯和碳青霉烯类抗生素关键中间体4-乙酰氧基氮杂环丁酮(4-AA). 该路线立体选择性非常好, 避免了手性异构体的分离和重金属盐的使用, 总收率30%. 中间体及产品4-AA的结构均通过IR, MS, H NMR和C NMR确认.

关键词: 青霉烯, 碳青霉烯, 4-乙酰氧基氮杂环丁酮, 6,6-二溴青霉烷酸甲酯, 立体选择性合成

The key intermediate of penem and carbapenem antibiotics 4-acetoxyazetidione (4AA) was obtained from methyl 6,6-dibromopenicillanate via oxidation, Grignard reaction, reduction, hydroxyl protection, ring opening reaction, methylation, deprotection and acetylation. This process avoided the separation of chiral isomers and the use of heavy metallic salt with an excellent stereoselectivity. The overall yield was 30%. The structures of the products were characterized by IR, MS, H NMR and C NMR techniques.

Key words: penem, carbapenem, 4-acetoxyazetidione, methyl 6,6-dibromopenicillanate, stereoselective synthesis