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

Abstract

807 1 DP, U. K, 1,4-Diaminoanthraquinone [leuco derivative (411 with aldehydes in the presence of 1,8-diazabicyclo[5.4.O]undec-7-ene in dimethyl formamide afforded (after aerial oxidation) 2-(hydroxyalkyl)-l,4-diaminoanthraquinones in good yields; reaction of (4) with 1,2-U-isopropylidene-3-U-methyl-cx-~-xylopentod~aldo-l,4-furanose (8) gave, stereospecifically, the hydroxyglycityl derivative (9) which was readily transformed into the novel 6,ll -diaminoanthracyclinone (12).