2-Acetyl-1,4-dihydroxyanthracene-9,10-dione 1 is converted into (±)-demethoxydaunomycinone by substitution with 3,3-dimethoxy-1-nitrobutan-2-one, aldol cyclisation, reduction and hydrolysis. The chiral inductions at C-10 realised on cyclisation of 5 and 8 are reported and the predominant chirality established.
K. Carr, N. A. Greener, K. B. Mullah, F. M. Somerville and J. K. Sutherland, J. Chem. Soc., Perkin Trans. 1, 1992, 1975 DOI: 10.1039/P19920001975
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