CYCLISCHE TRIKETONVERBINDUNGEN UND TRIMETHYLSILYLBUTADIENVERBINDUNGEN UND IHRE VERWENDUNG ZUR HERSTELLUNG VON DAUNOMYCINON-DERIVATEN

• Main Authors: SCHEEREN, JOHAN WILHELM, NL-6581 CL MALDEN, NL, DE BIE, JOANNES FRANCISCUS MARTINUS, NL-6521 ER NIJMEGEN, NL, DE VOS, DIRK, NL-2341 LP OEGSTGEEST, NL
• Format: Patent
• Language: German
• Published: 16.09.1993
• Edition: 5
• Subjects: ACYCLIC OR CARBOCYCLIC COMPOUNDS; ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAININGELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN,SULFUR, SELENIUM OR TELLURIUM; CHEMISTRY; METALLURGY; ORGANIC CHEMISTRY

The invention provides novel cyclic triketone compounds of the formulae wherein S is H, alkyl or alkoxy and R* is a group of the formule wherein R is methyl and R2 is an alkyl group containing at least 2 carbon atoms, or R is an alkyl group having 1-4 carbon atoms and R is an aryl group, a hetero aryl group, a -CH2OR min , a -CH2N @@ group, a -CH2SR sec group or a -CH2CH=CH2 group, wherein R min and R sec are alkyl groups having 1-4 carbon atoms. These compounds can be used for preparing daunomycinone and derivatives thereof. Daunomycinone is used for preparing daunomycin and adriamycin. By introducing chirality at C-1 of ring A in the preparation of said novel compounds by using a novel diene of formula (1) in a Diels-Alder reaction for said preparation, the chirality of C-3 is established in the subsequent reaction with LiC IDENTICAL CSi(CH3)3 in the synthesis of daunomycinone and derivatives thereof. This last reaction leads to the desired compound wherein OH at C-3 and OR at C-1 are in the cis-position with respect to each other.