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The preparation and oxidative demethylation attempts of podands 3--5, and 9 containing the 2,5-dimethoxyphenyl substituent are described. The reaction of alizarine 13 with chloroethanol afforded compounds 14 and 15. The pathway formation of heterocycle 15 from 14 is proposed. The synthesis of podand 16 containing the cytotoxic 1-hydroxy-9,10-anthraquinone fragment as the terminal groups is reported.
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