Chiral synthesis of anthracyclines from substituted anthraquinon

Details Chiral synthesis of anthracyclines from substituted anthraquinon Chiral synthesis of anthracyclines from substituted anthraquinon

1988-04-11

1990-11-27

Griffin, Ronald W.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

536 553, C07H 15244

Patent

active

049736744

ABSTRACT:
Anthracycline glycosides of formula (I): ##STR1## wherein R.sub.1 and R.sub.2 are independently selected from hydrogen, methyl, ethyl or methoxy and pharmaceutically acceptable acid addition salts thereof, which are useful in treatment of human cancer, are prepared by a stereospecific condensation of a derivative of daunosamine of general formula (II): ##STR2## wherein R.sub.3 is an alkyl, perfluoroalkyl or aryl group and R.sub.4, R.sub.5, R.sub.6 and R.sub.7 are independently selected from alkyl, aryl or aralkyl having up to ten carbon atoms, with a quinone quinizarine epoxide of general formula (III) ##STR3## and conversion of the product obtained to the anthracycline glycoside of formula (I) or salt thereof.

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