Cyclic triketone compounds and trimethylsilyoxy butadiene compou

Details Cyclic triketone compounds and trimethylsilyoxy butadiene compou Cyclic triketone compounds and trimethylsilyoxy butadiene compou

1991-12-20

1993-02-02

Shaver, Paul F.

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

Organic compounds

Silicon containing

556423, 556427, 556448, C07F 708, C07F 710, C07F 718

Patent

active

051839130

ABSTRACT:
The invention provides novel cyclic triketone compounds of the formulae ##STR1## wherein S is H, alkyl or alkoxy and R* is a group of the formule ##STR2## wherein R.sup.1 is methyl and R.sub.2 is an alkyl group containing at least 2 carbon atoms or R.sup.1 is an alkyl group having 1-4 carbon atoms and R.sup.2 is an aryl group, a hetero aryl group, a --CH.sub.2 OR' group, a --CH.sub.2 N<group, a --CH.sub.2 SR" group or a --CH.sub.2 CH.dbd.CH.sub.2 group, wherein R' and R" 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.tbd.CSi(CH.sub.3).sub.3 in the synthesis of daunomycinone and deriviatives thereof. ##STR3## 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.

REFERENCES:
patent: 4772683 (1988-09-01), Martel et al.
patent: 5061817 (1991-10-01), Ohashi et al.

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