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

Chin. J. Org. Chem. ›› 2010, Vol. 30 ›› Issue (07): 1017-1020. Previous Articles Next Articles

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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

(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

Abstract

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

Cite this article

XU Xiao-Bo, YANG Ying-Bin, DENG Qin, XIANG Li, XIANG Jian-Nan. Stereoselective Synthesis of 4-Acetoxyazetidione: the Key Intermediate of Penem and Carbapenem Antibiotics[J]. Chin. J. Org. Chem., 2010, 30(07): 1017-1020.

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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

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

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