Synthesis of 3,4-dioxocularine and aristocularine alkaloids in a convergent route from aryloxy-phenyl acetamides involving oxalyl chloride-Lewis Acid

@article{Suau2002SynthesisO3,
  title={Synthesis of 3,4-dioxocularine and aristocularine alkaloids in a convergent route from aryloxy-phenyl acetamides involving oxalyl chloride-Lewis Acid},
  author={R. Suau and R. Rico and J. M. L{\'o}pez-Romero and F. Najera and A. Ruiz and Francisco Javier Ortiz-L{\'o}pez},
  journal={Arkivoc},
  year={2002},
  volume={2002}
}
  • R. Suau, R. Rico, +3 authors Francisco Javier Ortiz-López
  • Published 2002
  • Chemistry
  • Arkivoc
  • Double cyclization of aryloxy-phenyl acetamides is promoted by oxalyl chloride/stannyl chloride and gives 3,4-dioxocularine and aristocularine alkaloids. Rearrangement of the dibenzoxepine ring prior to the second cyclization produces xanthene derivatives. The synthesized cularinoids exhibit significant activity against various tumoral cell lines. 
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    References

    SHOWING 1-10 OF 19 REFERENCES
    The isoquinoline alkaloids
    • 372
    Encyclopedia Reagents in organic synthesis
    • 244
    04) nm; HRMS calcd. for C 16 H 12 O 4 (M + ) m/z 268.0736, found 268.0735. 2,3-Methylenedioxy-5-methoxyxanthone (11b)
    • H-NMR δ (CDCl 3 ) 7.89 (1H, m, Ar-H), 7.64 (1H, s
    08) nm; Anal. Calcd. for C 18 H 13 NO 5 : C 66
    • UV (EtOH) (log ε) 412 (3.27)
    3-Methylenedioxy-5-methoxy-9-methylenexanthene (10b). Syrup, 0.035 g, quantitative; 1 H-NMR δ (CDCl 3 ) 7.28 (1H, dd
    • After refluxing for 12 h, the solution was diluted with wet THF and filtered. The filtrates were washed with water, dried and concentrated in vacuo to obtain 10b. This compound decomposes in air to 11b
    34) nm; Anal. Calcd. for C 17 H 15 NO 3 : C 73
    • UV
    90) nm; HRMS calcd
    • C 15 H 10 O 5 (M + ) m/z 270.0528
    91 (3H, s, OMe), 3.86 (3H, s, OMe), 3.82 (3H, s, OMe), 3.21 (3H, s, NMe); 13 C-NMR δ
      Ar-H), 5.70 (1H, s, H-α), 3.89 (3H, s, OMe), 3.20 (3H, s, NMe); 13 C-NMR δ
      • CDCl 3 ) 7.28 (1H, d, J=8.4, Ar-H), 7.1-6.9 (4H, m, Ar-H), 6.89 (1H, d, J=8
      Ar-H), 6.68 (1H, s, H-α), 4.04 (3H, s, OMe), 3.66 (3H, s, NMe); 13 C-NMR δ
      • Ar-H), 7.36-7.16 (4H, m