A new catalytic synthesis of the Wong's ant.racyclines intermediate, (R)-2-acetyl-2-hydroxy-5,8-dimethoxy-1,2,3,4-tetrahydronapthlene, starting from the corresponding 1,2-diol has been discovered through its selective hydrogenolysis in the presence of palladium heterogeneous catalysts. High yield and no racemization were found under mild reaction conditions: the molar selectivity towards the target product was always higher than 99.5%. The catalytic performances resulted strongly dependent on the nature of the palladium catalyst, unreduced Pd/C showing the best performances. This straightforward catalytic route significantly improves the up to now adopted industrial process. (c) 2006 Elsevier B.V. All rights reserved.
Catalytic hydrogenation for the industrial synthesis of the Wong's anthracyclines intermediate
RASPOLLI GALLETTI, ANNA MARIA;
2006-01-01
Abstract
A new catalytic synthesis of the Wong's ant.racyclines intermediate, (R)-2-acetyl-2-hydroxy-5,8-dimethoxy-1,2,3,4-tetrahydronapthlene, starting from the corresponding 1,2-diol has been discovered through its selective hydrogenolysis in the presence of palladium heterogeneous catalysts. High yield and no racemization were found under mild reaction conditions: the molar selectivity towards the target product was always higher than 99.5%. The catalytic performances resulted strongly dependent on the nature of the palladium catalyst, unreduced Pd/C showing the best performances. This straightforward catalytic route significantly improves the up to now adopted industrial process. (c) 2006 Elsevier B.V. All rights reserved.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
