Experiments directed towards the synthesis of anthracyclinones. VIII. Functionalization of hydroxyanthraquinones by reductive Claisen rearrangements

…, PJ Boniface, RC Cambie, PA Craw, Z Huang…

Index: Boddy, Ian K.; Boniface, Peter J.; Cambie, Richard C.; Craw, Peter A.; Huang, Zhen-Dong; et al. Australian Journal of Chemistry, 1984 , vol. 37, # 7 p. 1511 - 1529

Full Text: HTML

Citation Number: 13

Abstract

Abstract 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.

Related Articles:

First TDAE approach in quinonic series: Synthesis of new 2-substituted 1, 4-dimethoxy-9, 10-anthraquinones

[Khoumeri, Omar; Montana, Marc; Terme, Thierry; Vanelle, Patrice Tetrahedron, 2008 , vol. 64, # 49 p. 11237 - 11242]

Total synthesis and biological evaluation of (+)-and (−)-bisanthraquinone antibiotic BE-43472B and related compounds

[Mal, Dipakranjan; Ray, Sutapa; Sharma, Indrajeet Journal of Organic Chemistry, 2007 , vol. 72, # 13 p. 4981 - 4984]

Metal template ortho-acylation of phenols; A new general approach to anthracyclinones

[Sartori, Giovanni; Casnati, Giuseppe; Bigi, Franca; Robles, Pasquale Tetrahedron Letters, 1987 , vol. 28, # 14 p. 1533 - 1536]

C-Alkylation of Methyl leuco-6-Deoxykermesate by Aldol Reactions and its Application to Synthesis of Carminic Acid

[Bingham, Steve J.; Tyman, John H. P.; Malik, K. M. A.; Hibbs, David E.; Hursthouse, Michael B. Journal of Chemical Research, Miniprint, 1998 , # 9 p. 2465 - 2496]

Total synthesis and biological evaluation of (+)-and (−)-bisanthraquinone antibiotic BE-43472B and related compounds

[Mal, Dipakranjan; Ray, Sutapa; Sharma, Indrajeet Journal of Organic Chemistry, 2007 , vol. 72, # 13 p. 4981 - 4984]

More Articles...