Chin. J. Org. Chem. ›› 2009, Vol. 29 ›› Issue (02): 252-258. Previous Articles     Next Articles

Original Articles

螺[1-溴-4-甲氧基-5-氧杂-6-氧代双环[3.1.0]己烷-2,2¢-(3-{α-[二(乙氧基)膦酸酯基]苄氧基}-4-甲氧基-5-氧杂-1-氧代环戊烷)]的合成、 结构及抗肿瘤活性的研究

裴 强* ; 金春雪 ; 牛满丽; 程志红   

  1. (信阳师范学院化学化工学院 信阳 464000)
  • 收稿日期:2008-05-14 修回日期:2008-07-24 发布日期:2009-02-20
  • 通讯作者: 裴 强

Synthesis, Structure and Anti-tumor activity of Spiro[(1-bromo-4-me- thoxy-5-oxa-6-oxobicyclo[3.1.0]hexane-2,2’-(3-{α-[di(ethoxy)phos- phoryl]benzyloxy}-4-methoxy-5-oxa-1-oxocyclopentane]

Pei, Qiang*; Jin, Chunxue; Niu, Manli; Cheng, Zhihong   

  1. (Department of Chemistry, Xinyang Normal University, Xinyang 464000)

  • Received:2008-05-14 Revised:2008-07-24 Published:2009-02-20
  • Contact: Pei, Qiang

Racemic diastereoisomeric spiro-phosphonate derivatives 5~6 were obtained by tandem double Michael addition and intramolecular nucleophilic substitution of 3-bromo-5-methoxy-5H-furan-2-one and α-hydroxylbenzylphosphonate under a warm condition. The target compounds 5~6 were identified by the elemental analysis, IR, 1H NMR, 13C NMR and MS techniques. The stereochemistry and configuration of 5c and 6c were confirmed further by X-ray crystallography. This result could lead to a new strategy for the synthesis of some complicated compounds containing a phosphorus functional group.

Key words: spiro-phosphonate derivate, X-ray crystallography, anti-tumor activity, tandem asymmetric reaction