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

  title={Synthesis of 3,4-dioxocularine and aristocularine alkaloids in a convergent route from aryloxy-phenyl acetamides involving oxalyl chloride-Lewis Acid},
  author={Rafael Suau and Rodrigo Rico and Juan Manuel L{\'o}pez-Romero and Francisco N{\'a}jera and Antonio S{\'a}nchez Ruiz and Francisco Javier Ort{\'i}z-L{\'o}pez},
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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Encyclopedia Reagents in organic synthesis

Z:E mixture, 3:2.5); 1 H-NMR  δ (CDCl 3 ) Mayor isomer (Z)

  • CHCl

OMe), 3.92 (3H, s, OMe), 3.84 (3H, s, OMe), 3.66 (3H, s, NMe); 13 C-NMR δ (CDCl 3 ) 175.2 (C-4)

    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

    Orange solid, 0.084 g, 12%; mp 283-90 ºC

    • CHCl

    Starting products 4a-c were readily prepared by bromination (Br 2 /AcOH) of phenylacetic acid, 3,4-dimethoxyphenylacetic acid and 3,4-methylenedioxy

      90) nm; HRMS calcd

      • C 15 H 10 O 5 (M + ) m/z 270.0528

      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

      Red amorphous solid, 0.27 g, 40%; mp 180-3 ºC