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A Convergent Route for the Synthesis of AF-5

A Convergent Route for the Synthesis of AF-5
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摘要 AF-5 was synthesized through a convergent method. The key step was the Robinson annulation using a key intermediate pentyl vinyl ketone. AF-5 was synthesized through a convergent method. The key step was the Robinson annulation using a key intermediate pentyl vinyl ketone.
作者 Da Li YIN Ji Yu GUO Xiao Tian LIANG
机构地区 Institute of Materia Medica
出处 《Chinese Chemical Letters》 SCIE CAS CSCD 2003年第7期670-672,共3页 中国化学快报(英文版)
基金 The authors gratefully acknowledge financial support from the National Natural Science Foundation of China(No.39370809) National New Drug Foundation(No.92-08-N).
关键词 AF-5 SYNTHESIS Robinson annulation. AF-5 synthesis Robinson annulation.
分类号 O621.3 [理学—有机化学]
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参考文献10

  • 1J. Y. Guo, W. J. Wang, H. J. Fang, et al., WO 00/31058, 2000.
  • 2W. Y. Zhang, J. Y. Guo, X. T. Liang, Chin. Chem. Lett., 2000, 11(5), 399.
  • 3H. C. Barrett, G. Büchi, J. Am.Chem. Soc., 1967, 89, 5663.
  • 4J. A. Marshall, M. T. Pike, J. Org. Chem., i968, 33(1), 435.
  • 5G. Büchi, H. Wriest, J. Org. Chem., 1979, 44(4), 546.
  • 6J. W. Huffman, R. C. Desk, J. Orgl Chem., 1982, 47, 3254.
  • 7oil,^1H NMR(CDCl3,δ ppm): 0.89(t, 3H, J=7.2), 1.29(m, 4H), 1.62(m, 2H), 2.22(s, 3H),2.52(t, 2H, J=7.4), 6.00(d, 1H, J=-12.8), 8.24(d, 1H, J=12.8). MS(EI):m/z 169(M+H).
  • 8oil IH NMR(CDCl3,δ ppm)i 0.88(t, 3H,J=7.2）, 1.29(m, 4H), 1.57(m, 2H), 2.01(s, 3H), 2.41(t,2H, J=7.6), 2.72(t, 2H, J=6.3), 4.31(t, 2H, J=6.3).
  • 9oil, ^1H NMR(CDCl3, δ ppm）:0.89（t,3H, J=7.2）, 1.30 (m, 4H), 1.60（m, 2H）, 2.58(t, 214, J=4.8), 5.81(dd, 1H, J=10.5,1.4),6.21(dd,1H, J=17.7, 1.4), 6.35(dd, 1H, J=17.7, 10.5).
  • 10oil, ^1H NMR(CDCl3, δ ppm): 0.87(t, 3H J=7.2), 1.03(s, 3H), 1.15-1.35(m, 4H), 1.45-1.70(m, 4H), 1.75(s, 3H), 1.70-1.90(m, 3H),2.05-2.20(m, 3H), 2.30-2.50(m, 5H), 4.71(s, 1H), 4.76(s, 1H). The ^1H NMR data of compounds 10,11 and 12 are identical with those in reference2.
Chinese Chemical Letters
2003年 第7期

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