
%0 Journal Article
%A Bercich, Mark D. 
%A Cambie, Richard C. 
%A Rutledge, Peter S. 
%T Experiments Directed Towards the Synthesis of Anthracyclinones. XXXII. Synthesis of Anthraquinone Aldehydes
%J Australian Journal of Chemistry
%D 1999/05/27
%V 52
%N 4
%P 241-258
%K 
%R https://doi.org/10.1071/C98102
%U https://www.publish.csiro.au/paper/C98102 
%X Syntheses of C2 anthraquinone aldehydes from the commercially availableanthraru&#175;n (1) have been investigated. A synthesis of the keto aldehyde(2) in nine steps and 73% overall yield was achieved. Syntheses of (2)exploiting selective oxidations of either a C-boundallyl group by Wacker oxidation to introduce the methyl keto functionality orof a C-bound prop-1-enyl moiety by dihydroxylation andoxidative cleavage to generate the C2 formyl group were also developed. Thealdehyde (27) was synthesized in seven steps and in 81% overall yieldfrom (1), and syntheses of the phenolic aldehydes (33), (34), and (35), the C1benzyloxy aldehyde (36) and the anthracene aldehyde (37) were also developed. 
