TY - JOUR
T1 - Nuclear alkylation of 1,4-diaminoanthraquinone. Synthesis of chiral 6,11-diaminoanthracyclinones related to ametantrone from carbohydrates
AU - Mills, Susan K
AU - Mincher, David J
AU - Shaw, Gordon
PY - 1988
Y1 - 1988
N2 - 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).
AB - 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).
UR - http://www.scopus.com/inward/record.url?scp=0009483573&partnerID=8YFLogxK
U2 - 10.1039/C39880000399
DO - 10.1039/C39880000399
M3 - Article
SN - 0022-4936
SP - 399
EP - 401
JO - Journal of the Chemical Society, Chemical Communications
JF - Journal of the Chemical Society, Chemical Communications
IS - 5
ER -