Intermediates for (1,5) 6,6-Dimethyl-4-Hydroxy-3-oxabicyclo (3,1

Details Intermediates for (1,5) 6,6-Dimethyl-4-Hydroxy-3-oxabicyclo (3,1 Intermediates for (1,5) 6,6-Dimethyl-4-Hydroxy-3-oxabicyclo (3,1

1987-04-10

1989-01-31

Fan, Jane T.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D30758

Patent

active

048017230

ABSTRACT:
A process for the preparation of compounds of the (1RS, 4RS, 5SR), (1R, 4R, 5S) or (1S, 4S, 5R) configuration having the formula ##STR1## wherein Y is selected from the group consisting of hydrogen and the organic residue Z of an optionally chiral alcohol of the formula ZOH comprising reacting in the presence of an acid agent 5RS-hydroxy-2,5-dihydrofuran-2-one having the formula ##STR2## either (a) with an achiral alcohol of the formula ZOH to obtain the resulting ether and reacting the latter in an anhydrous medium with an isopropylidene sulfurane of the formula ##STR3## wherein R.sub.1 and R.sub.2 are individually selected from the group consisting of optionally substituted monocyclic aromatic groups, isopropyl, groups and tertiary alkyl groups, to obtain a compound of formula I of the (1RS, 4RS, 5SR) configuration and Y is Z and optionally hydrolyzing the latter in acid medium to obtain the compound of formula I wherein Y is hydrogen or (b) with an optically active chiral alcohol of the formula ZOH to obtain a mixture of stereoisomeric ether due to the asymetrical carbon in the 5-position which mixture is rich in one of the two diastereoisomers, separating the diastereoisomeric ethers by physical means and reacting the separated diastereoisomers with the compound of formula II in anhydrous medium to obtain the compound of formula I with (1R, 4R, 5S) or (1S, 4S, 5R) configuration wherein Y is Z and optionally hydrolyzing the latter in an acid media to obtain the compound of formula I wherein Y is hydrogen and novel intermediates. The compounds of formula I where Y is hydrogen are described in French Pat. No. 1,580,474 and are interemediates for diversely substituted cyclopropane carboxylic acids whose esters are may active insecticides.

REFERENCES:
Kaeriyama et al., CA 87:39258M.
Fuchs et al., CA 63:6851a.
CA 63:11352g.
Hashimoto et al., CA 86:71934u.
Merwe et al., CA 62:9088e.

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