Towards a versatile synthesis of kainoids III: Efficient methods for control of C-4 stereochemistry

Tetrahedron

Volumn 53, Issue 14, 1997, Pages 5273-5290

  Baldwin, Jack E ^a   Fryer, Andrew M ^a   Spyvee, Mark R ^a   Whitehead, Roger C ^b   Wood, Mark E ^c  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b UNIVERSITY OF READING   (United Kingdom)

^c UNIVERSITY OF EXETER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

DICARBOXYLIC ACID DERIVATIVE; LACTONE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0030971996     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00192-0     Document Type: Article

References (12)

1. See previous two papers in this issue.
2. Gonzalez, F. B.; Bartlett, P. A. Org. Synth., Coll. Vol. VII, 1990, 164-167.
3. 2
4. Jew, S.-S.; Terashima, S.; Koga, K. Tetrahedron, 1979, 35, 2337-2343.
5. Nicolaou, K.C. Tetrahedron, 1981, 37, 4097-4109.
6. Shioiri, T.; Aoyama, T. Chem. Pharm. Bull., 1991, 29, 3249-3255.
7. Khan, A. M.; McQuillin, F. J.; Jardine, I. J. Chem. Soc. (C), 1967, 136-139.
8. For example, see: Kunzer, H.; Sauer, G.; Wiechert, R. Tetrahedron Lett., 1991, 32, 743-746.
9. Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem., 1981, 46, 3936-3938.
10. Jones oxidation method used was identical to that used in a synthesis of (-)-α-kainic acid except for an extended reaction time (18h); Cooper, J.; Knight, D. W.; Gallagher, P. T. J. Chem. Soc., Perkin Trans. I, 1992, 553-559.
11. Marino, J. P.; de la Pradilla, R. F.; Laborde, E. J. Org. Chem., 1987, 52, 4898-4913.
12. Derome, A. E., Modern NMR Techniques for Chemistry Research, Pergamon Press, Oxford, 1987.