CYCLISCHE TRIKETONVERBINDINGEN EN TRIMETHYLSILYLOXYBUTADIEENVERBINDINGEN EN HUN TOEPASSING BIJ HET BEREIDEN VAN DAUNOMYCINONDERIVATEN.

摘要

The invention provides novel cyclic triketone compounds of the formulae CHEM wherein S is H, alkyl or alkoxy and R* is a group of the formule CHEM wherein R1 is methyl and R2 is an alkyl group containing at least 2 carbon atoms, or R1 is an alkyl group having 1-4 carbon atoms and R2 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. CHEM 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.