Cyclic triketone compounds and trimethylsilyloxy butadiene compo

Details Cyclic triketone compounds and trimethylsilyloxy butadiene compo Cyclic triketone compounds and trimethylsilyloxy butadiene compo

1990-02-01

1992-03-17

Shaver, Paul F.

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

Organic compounds

Polycyclo ring system containing anthracene configured ring...

C07C 3917

Patent

active

050970518

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 derivatives 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: 4405522 (1983-09-01), Mitscher

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