C - Chemistry – Metallurgy – 07 – C
Patent
C - Chemistry, Metallurgy
07
C
260/208, 260/236
C07C 50/38 (2006.01) C07C 225/32 (2006.01) C07F 7/08 (2006.01) C07F 7/18 (2006.01)
Patent
CA 2009096
S 5719-4 Can Abstract of the disclosure The invention provides novel cyclic triketone ccmpounds of the formulae Image Image (2) (3) wherein S is H, alkyl or alkoxy and R* is a group of the formule Image wherein R1 is methyl and R2 is an alkyl group containing at least 2 car- bon atoms or R1 is an alkyl group having 1-4 carbon atoms and R2 is an aryl group, a hetero aryl group, a -CH2OR' group, a Image group, a -CH2SR" group or a -CH2CH=CH2 group, wherein R' and R" are alkyl groups having 1-4 carbon atoms. These compounds can be used for preparing daunomycinone and deri- vatives thereof. Daunomycinone is used for preparing daunomycin and ad- riamycin. 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=CSi(CH3)3 in the synthesis of dauno- mycinone and derivatives thereof.
de Bie Joannes F. M.
de Vos Dirk
Scheeren Johan W.
Gowling Lafleur Henderson Llp
Pharmachemie B.v.
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