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

Susan K Mills, David J Mincher, Gordon Shaw

Research output: Contribution to journalArticle

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-a-D- xylopentodialdo-1,4-furanose (8) gave, stereospecifically, the hydroxyglycityl derivative (9) which was readily transformed into the novel 6,11- diaminoanthracyclinone (12).

Original languageEnglish
Pages (from-to)399-401
Number of pages3
JournalJournal of the Chemical Society, Chemical Communications
Issue number5
DOIs
Publication statusPublished - 1988

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