
%0 Journal Article
%A Cambie, RC 
%A Larsen, DS 
%A Rickard, CEF 
%A Rutledge, PS 
%A Woodgate, PD 
%T Experiments Directed Towards the Synthesis of Anthracyclinones. X. A Synthesis of (&plusmn;)-4-Demethoxydaunomycinone
%J Australian Journal of Chemistry
%D 1986/03/01
%V 39
%N 3
%P 487-502
%K 
%R https://doi.org/10.1071/CH9860487
%U https://www.publish.csiro.au/paper/CH9860487 
%X The acetal methyl 2-(3-dimethoxymethyl-4-hydroxy-1-methoxy-9,10-dioxo- 9,10-dihydroanthracen-2-yl)acetate (2), a versatile intermediate prepared earlier from quinizarin (1), has been converted into (±)-4- demethoxydaunomycinone (5) in 43% yield (on a small scale) from the acetal (2) and in 29% overall yield from quinizarin. The structure of (±)-9&#945;-acetyl-6,9-dihydroxy-7&#945;,11-dimethoxy-5,7,8,9,10,12-hexahydronaphthacene-5,12-dione (6), an intermediate in the sequence, has been confirmed by X-ray studies. 
