An efficient synthesis of (S)-m-tyrosine

Journal of Organic Chemistry

Volumn 62, Issue 19, 1997, Pages 6690-6691

  Bender, David M ^a   Williams, Robert M ^a  

^a Immunology and Pathology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYL ALCOHOL DERIVATIVE; LEVODOPA; META TYROSINE; MUREIDOMYCIN A; OXAZINE DERIVATIVE; PROTEINASE INHIBITOR; TETRAHYDROFURAN;

ARTICLE; DRUG PURITY; DRUG SYNTHESIS; ENANTIOMER; GAS CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE; PARKINSON DISEASE; STEREOCHEMISTRY;

EID: 0030802675     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9706584     Document Type: Article

References (23)

1. (a) Sealock, R. R.; Speeter, M. E.; Schweet, S. J. Am. Chem. Soc. 1951, 73 5386;
2. (b) Tong, J. H.; Petitclerc, C.; D'Iorio, A.; Benoiton, N. L. Can. J. Biochem. 1971, 49, 877.
3. (c) Smith, I. K.; Fowden, L. Phytochemistry 1968, 7, 1065.
4. (d) Byrkjedal, A.; Mostad, A.; Romming, C. Acta Chem. Scand. 1974, B28, 750.
5. (a) Hollunger, G.; Persson, S.-A. Acta. Pharmacol Toxicol. 1974, 34, 391.
6. (b) Fell, V.; Greenway, A. M.; Hoskins, J. A. Biochem. Med. 1979, 22, 246.
7. Ungerstedt, U.; Fuxe, K.; Goldstein, M.; Battista, A.; Ogawa, M.; Anagnoste, B. Eur. J. Pharmacol. 1973, 21, 230.
8. (a) Inukai, M.; Isono, F.; Takahashi, S.; Enokita, R.; Sakaida, Y.; Haneishi, T. J. Antibiot. 1989, 42, 662.
9. (b) Isono, F.; Inukai, M.; Takahashi, S.; Haneishi, T. J. Antibiot. 1989, 42, 667.
10. (c) Isono, F.; Katayama, T.; Inukai, M.; Haneishi, T. J. Antibiot. 1989, 42, 674.
11. (a) Karwowski, J. P.; Jackson, M.; Theriault, R. J.; Chen, R. H.; Barlow, G. J.; Maus, M. L. J. Antibiot. 1989, 42, 506.
12. (b) Chen, R. H.; Buko, A. M.; Whittern, D. N.; McAlpine, J. B. J. Antibiot. 1989, 42, 512.
13. (c) Fernandas, R. B.; Swanson, R. N.; Hardy, D. J.; Hanson, C. W.; Coen, L.; Rasmussen, R. R. J. Antibiot. 1989, 42, 521.
14. Chen, P.; Cheng, P. T. W.; Alam, M.; Beyer, B. D.; Bisacchi, G. S.; Dejneka, T.; Evans, A. J.; Greytok, J. A.; Hermsmeier, M. A.; Humphreys, W. G.; Jacobs, G. A.; Kocy, O.; Lin, P.-F.; Lis, K. A.; Marella, M. A.; Ryono, D. E.; Sheaffer, A. K.; Spergel, S. H.; Sun, C.-q.; Tino, J. A.; Vite, G.; Colonno, R. J.; Zahler, R.; Barrish, J. C. J. Med. Chem. 1996, 39, 1991.
15. Dugave, C., J. Org. Chem. 1995, 60, 601.
16. For reviews on methods to prepare α-amino acids, see: (a) Williams, R. M. Organic Chemistry Series, Vol. 7: Synthesis of Optically Active α-Amino Acids; Baldwin, J. E., Magnus, P. D., Eds.; Pergamon Press, Oxford, 1989. (b) Duthaler, R. O., Tetrahedron 1994, 50, 1539.
17. For reviews on methods to prepare α-amino acids, see: (a) Williams, R. M. Organic Chemistry Series, Vol. 7: Synthesis of Optically Active α-Amino Acids; Baldwin, J. E., Magnus, P. D., Eds.; Pergamon Press, Oxford, 1989. (b) Duthaler, R. O., Tetrahedron 1994, 50, 1539.
18. Both antipodes of 3 are commercially available from Aldrich Chemical Co.: 3, catalog #33,187-2; antipode of 3, catalog #33-185-6.
19. (a) Williams, R. M.; Im, M.-N. Tetrahedron Lett. 1988, 29, 6075.
20. (b) Williams, R. M.; Im, M.-N. J. Am. Chem. Soc. 1991, 113, 9276.
21. (c) Williams, R. M. Aldrichimica Acta 1992, 25, 11.
22. Dale, J. A.; Hull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543.
23. For general experimental conditions, see ref 10b.