Protected 5,7-dihydroxy-4,4-dimethyl-3-oxoheptanoic acid esters and 5,7-dihydroxy-2-alkyl-4,4-dimethyl-3-oxoheptanoci acid esters for the synthesizing of epothilone and epothilone derivatives and process for the production of these esters
View Patent ↗This invention describes protected 5,7-dihydroxy-4,4-dimethyl-3-oxoheptanoic acid ester and 5,7-dihydroxy-2-alkyl-4,4-dimethyl-3-oxoheptanoic acid ester for the synthesis of epothilones and epothilone derivatives and process for the production of these esters.
1. A compound of formula V
in which
PG 1 and PG 2 stand for hydroxy protective groups or together for an isopropylidene group, and
R 1 stands for a straight-chain or branched-chain, optionally unsaturated hydrocarbon radical with up to 6 carbon atoms.
2. A compound of formula VI
PG 1 and PG 2 stand for hydroxy protective groups or together for an isopropylidene group, and
R 1 stands for a straight-chain or branched-chain, optionally unsaturated hydrocarbon radical with up to 6 carbon atoms, and R 6 stands for a C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl or C 2 -C 6 -alkinyl radical, which can be straight-chain or branched, or for an alkoxyalkyl, alkoxy-alkenyl, alkoxyalkinyl or aryl-alkyl radical, in which alkyl in the alkoxy portion means a C 1 -C 6 -alkyl radical and aryl means a phenyl or naphthyl radical, and alkyl-, alkenyl-, alkinyl mean a C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl or C 2 -C 6 -alkenyl radical.
3. A compound of formula VII
in which
PG 1 and PG 2 stand for hydroxy protective groups or together for an isopropylidene group, and
R 6 stands for a C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl or C 2 -C 6 -alkinyl radical, which can be straight-chain or branched, or for an alkoxyalkyl, alkoxy-alkenyl, alkoxyalkinyl or aryl-alkyl radical, in which alkyl in the alkoxy portion means a C 1 -C 6 -alkyl radical and aryl means a phenyl or naphthyl radical, and alkyl-, alkenyl-, alkinyl mean a C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl or C 2 -C 6 -alkenyl radical
and
M stands for a lithium atom or the radical MgX with X in the meaning of a chlorine, bromine or iodine atom.
4. A compound of formula IX
in which
PG 1 and PG 2 stand for hydroxy protective groups or together for an isopropylidene group, and
R b stands for a hydrogen atom or a straight-chain or branched-chain C 1 -C 6 -alkyl radical.