128885-71-2Relevant articles and documents
Syntheses Totales d'Oxa-9 anthracyclines
Dufat-Trinh, Hahn van,Seguin, Elisabeth,Tillequin, Francois,Monneret, Claude,Koch, Michel
, p. 3294 - 3300 (2007/10/02)
Racemic 7-hydroxy-9-oxa-anthracyclinone (5a) has been synthetised in seven steps from quinizarin (6) and its resolution achieved after glycosylation with 3,4-di-O-acetyl-2-deoxy-L-fucose.Chiral pool syntheses of (8S)-8-hydroxymethyl-9-oxa-anthracyclinone (5b) and of (8S,10R) and (8S,10S)-8-hydroxymethyl-10-methyl-9-oxa-anthracyclinones (5c and 5d) have been achieved using (R)-2,3-O-isopropylideneglyceraldehyde (12) and leucoquinizarin (13) as starting materials.Glycosylation of aglycones 5b-5d by either 3,4-di-O-acetyl-2-deoxy-L-fucose or various 3-amino-2,3,6-trideoxy-L-hexoses yielded the corresponding anthracyclines.The synthetic glycosides do not show significant cytotoxic activity at a concentration of 1 μg/ml against L 1210 cells.Keywords 9-oxa-anthracyclinone; 9-oxa-anthracycline; glycoside; chiral pool synthesis