Issue 5, 1988

Nuclear alkylation of 1,4-diaminoanthraquinone. Synthesis of chiral 6,11-diaminoanthracyclinones related to ametantrone from carbohydrates

Abstract

1,4-Diaminoanthraquinone [leuco derivative (4)] with aldehydes in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene in dimethyl formamide afforded (after aerial oxidation) 2-(hydroxyalkyl)-1,4-diaminoanthraquinones in good yields; reaction of (4) with 1,2-O-isopropylidene-3-O-methyl-α-D-xylopentodialdo-1,4-furanose (8) gave, stereospecifically, the hydroxyglycityl derivative (9) which was readily transformed into the novel 6,11-diaminoanthracyclinone (12).

Article information

Article type
Paper

J. Chem. Soc., Chem. Commun., 1988, 399-401

Nuclear alkylation of 1,4-diaminoanthraquinone. Synthesis of chiral 6,11-diaminoanthracyclinones related to ametantrone from carbohydrates

S. K. Mills, D. J. Mincher and G. Shaw, J. Chem. Soc., Chem. Commun., 1988, 399 DOI: 10.1039/C39880000399

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