Compounds useful as intermediates in the synthesis of shikimic a

Details Compounds useful as intermediates in the synthesis of shikimic a Compounds useful as intermediates in the synthesis of shikimic a

1992-08-24

1993-05-25

Lee, Mary C.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549546, C07C31708, C07C30340

Patent

active

052141659

ABSTRACT:
6-Fluoroshikimic acid derivatives of the formula (I): ##STR1## wherein R.sup.1 is hydroxy or a moiety biotransformable thereto and R.sup.2 is hydrogen or --P(O)(OH).sub.2 have antibacterial, antifungal and herbicidal activity. Their preparation and use are described as are pharmaceutical compositions containing them.

REFERENCES:
Pilch et al, Fluorine-Containing Analogues of Intermediates in the Shikimate, Biochemistry, vol. 15, No. 24, pp. 5315-5320, (1976).
Leroy et al, Stereospecific Synthesis of Racemic cis- and trans-6-Trifluoromethylshikimic Acids, J. Chem. Soc. Perkin Trans. 1, pp. 1281-1287, (1990).
Bundgarrd "Design of Prodrugs: Bioreversible Derivatives for Various Functional Groups and Chemical Entities", pp. 1 and; 2, Design of Prodrugs, Bungaard, ed. (1985) Elsevier Amsterdam.
Le Marechal, "Contribution to the Study of the Mechanism of Action of an Enzyme of the Aromatic Amino Acid biosynthetic Pathway; 3-Dehydroguinate Synthetase from Escherichia coli. Preparation and use of Analogues of 3-dexosy-D-arabino heptulosonate 7-phosphate, its substrate.", Thesis submitted at the University of Paris XI, Dentre D'Orsay to obtain the degree of Doctor of Natural Sciences by Pierre Le Marechal (1981).
Ganem, B. Tetrahedron 1978, 34 (23), 3353-83.
Bowles et al, "Reactivity Studies in the Shikimic Acid Series", Tetrahedron Letters, vol. 30, No. 28, pp. 3711-3714, 1989.
Le Marechal et al, The Shikimate Pathway V, Flourine-containing Analogues of 3-deoxy-D-arabino hept-2-ulsonate-7-phosphate (DAHP) Biochemie 1986, 68, 1211-1215.

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