Nuclear alkylation of 1,4-diaminoanthraquinone. Synthesis of chiral 6,11-diaminoanthracyclinones related to ametantrone from carbohydrates
- 1 January 1988
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 5,p. 399-401
- https://doi.org/10.1039/c39880000399
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).Keywords
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