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Experiments Directed Towards the Synthesis of Anthracyclinones. VIII* Functionalization of Hydroxyanthraquinones by Reductive Claisen Rearrangements

Tipo de material: TextoTextoSeries ; Australian Journal of Chemistry, 37(7), p.1511-1529, 1984Trabajos contenidos:
  • Boddy, I.K
  • Boniface, P.J
  • Cambie, R.C
  • Craw, P.A
  • Huang, Z
  • Larsen, D.S
  • Mcdonald, H
  • Mcdonald, H
  • Woodgate, P.D
Recursos en línea: Resumen: Gentle heating of allyloxyanthraquinones with sodium dithionite in dimethylformamide/water effects a rapid and controlled rearrangement to give high yields of 2-allylhydroxyanthraquinones. Starting from quinizarin, key intermediates for two synthetic routes to 4-demethoxydaunomycinone have been prepared from products by means of two such reductive Claisen rearrangements.
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Gentle heating of allyloxyanthraquinones with sodium dithionite in dimethylformamide/water effects a rapid and controlled rearrangement to give high yields of 2-allylhydroxyanthraquinones. Starting from quinizarin, key intermediates for two synthetic routes to 4-demethoxydaunomycinone have been prepared from products by means of two such reductive Claisen rearrangements.

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