Intermediates for the synthesis of kainic acid

Details Intermediates for the synthesis of kainic acid Intermediates for the synthesis of kainic acid

1994-04-22

1996-01-23

Haley, Jacqueline

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D51316

Patent

active

054866200

ABSTRACT:
This invention provides a process for preparing kainic acid and provides intermediates in the synthesis thereof.

REFERENCES:
Oppolzer and Andres, "A Total Synthesis of .alpha.-Kainic Acid by an Intramolecular Ene Reaction", Helv. Chim. Acta, 62, p. 2282 (1979).
Potts, Choudhury, and Westby, "Bridgehead Nitrogen Systems.X. Cycloadditions with Thiazolium N-Ylides.sup.1 ", J. Org. Chem., 41, p. 187 (1976).
Kraus and Nagy, "The synthesis of amino acids by 1,3-dipolar cycloadditions of azomethine ylides", Tetrahedron, 41, p. 3537 (1985).
Reetz, Kyung, and Hullman, "CH.sub.3 Li/TiCl.sub.4 : A non-basic and highly selective Grignard analogue", Tetrahedron, 42, No. 11 p. 2931 (1986).
Carlsen, Katsuki, Martin, and Sharpless, "A Greatly Improved Procedure for Ruthenium Tetraoxide Catalyzed Oxidations of Organic Compounds", J. Org. Chem., 46, p. 3936 (1981).
Hibino, Okazoe, Takai, and Nozaki, "carbonyl methylenation of easily enolizable ketones", Tetr. Lett., 26, p. 5579 (1985).
Takano, Sugihara, Satoh, and Ogasawara, "Enantioselective Synthesis of (-)-Kainic Acid", J. Am. Chem. Soc., 110, p. 6467 (1988).
Husinec, Porter, Roberts, and Strachan, "Some Approaches to the Synthesis of Kainic Acid", J. Chem. Soc., Perkin Trans. I, p. 2517 (1984).
Husinec, Porter, and Strachan, "Approaches to the synthesis of kainic acid. A study of the synthesis of some 4,5-dihydro-1,2,3-triazoles", Coll. Czech. Chem. Comm., 52 p. 207 (1987).
Murakami, Hasegawa, Hayashi, and Ito, "Synthesis of (.+-.)-a-Allokainic Acid via the Zinc Acetate Catalyzed Cyclization of .gamma.-Isocyano Silyl Enolates", J. Org. Chem., 56, p. 7356 (1991).
Takano, Inomata, and Ogasawara, "A New Enantiospecific Route to (-)-Kainic Acid via the Intramolecular Pauson-Khand Reaction", J. Chem. Soc., Chem. Comm., p. 169 (1992).
Green, T., Protective Groups in Organic Synthesis, John Wiley & Sons, Inc., New York, 1981, pp. 218-222.

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