Experiments Directed Towards the Synthesis of Anthracyclinones. VIII* Functionalization of Hydroxyanthraquinones by Reductive Claisen Rearrangements
Experiments Directed Towards the Synthesis of Anthracyclinones. VIII* Functionalization of Hydroxyanthraquinones by Reductive Claisen Rearrangements
- Australian Journal of Chemistry, 37(7), p.1511-1529, 1984 .
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.
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.