Facile synthesis of 3-hydroxyglutamic acids via cyanation of chiral N-acyliminium cation derived from (S)-malic acid

Synthetic Communications

Volumn 35, Issue 23, 2005, Pages 2961-2966

  Oba, Makoto ^a   Mita, Atsushi ^a   Kondo, Yoshinori ^a   Nishiyama, Kozaburo ^a  

^a TOKAI UNIVERSITY   (Japan)

Author keywords

3 hydroxyglutamic acid; Cyanation; Malic acid; N acyliminium cation

Indexed keywords

3 HYDROXYGLUTAMIC ACID; BORON TRIFLUORIDE; CYANIDE; IMINE; LACTAM DERIVATIVE; MALIC ACID; SODIUM BOROHYDRIDE; TRIMETHYLSILYL DERIVATIVE;

ACETYLATION; ARTICLE; CHEMICAL REACTION; CHROMATOGRAPHY; CYANATION; DIASTEREOISOMER; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 28444446719     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910500278446     Document Type: Article

References (24)

1. (a) Shimamoto, K.; Ishida, M.; Shinozaki, H.; Ohfune, Y. J. Org. Chem. 1991, 56, 4167-4176;
2. (b) Shimamoto, K.; Ohfune, Y. J. Med. Chem. 1996, 39, 407-423;
3. (c) Dinsmore, A.; Doyle, P. M.; Young, D. W. Tetrahedron Lett. 1995, 36, 7503-7506;
4. (d) Conti, P.; Dallanoce, C.; Amici, M. D.; Micheli, C. D.; Fruttero, R. Tetrahedron 1999, 55, 5623-5634;
5. (e) Kozikowski, A. P.; Steensma, D.; Araldi, G. L.; Tückmantel, W.; Wang, S.; Pshenichkin, S.; Surina, E.; Wroblewski, J. T. J. Med. Chem. 1998, 41, 1641-1650;
6. (f) Gu, Z.-Q.; Hesson, D. P.; Pelletier, J. C.; Maccecchini, M.-L. J. Med. Chem. 1995, 38, 2518-2520.
7. (a) Oba, M.; Koguchi, S.; Nishiyama, K. Tetrahedron Lett. 2001, 42, 5901-5902;
8. (b) Oba, M.; Koguchi, S.; Nishiyama, K. Tetrahedron 2002, 58, 9359-9363;
9. (c) Oba, M.; Koguchi, S.; Nishiyama, K. Tetrahedron 2004, 60, 8089-8092.
10. (a) Zhang, W.; Takeuchi, H.; Kurono, M. Gen. Pharmacology 1996, 27, 499-504;
11. (b) Watanabe, K.; Takeuchi, H.; Kurono, M. Eur. J. Pharmacol. 1985, 111, 57-63.
12. (a) Vidal-Cros, A.; Gaudry, M.; Marquet, A. J. Org. Chem. 1985, 50, 3163-3167;
13. (b) Kamiya, T. Chem. Pharm. Bull. 1966, 14, 1307-1309.
14. Shoji, J.; Salazaki, R. J. Antibiot. 1970, 23, 418-419.
15. (a) Veeresa, G.; Datta, A. Tetrahedron Lett. 1998, 39, 3069-3070;
16. (b) Dell'Uomo, N.; Giovanni, M. C. D.; Misiti, D.; Zappia, G.; Monache, G. D. Liebigs Ann. Chem. 1994, 641-644;
17. (c) Blaskovich, M. A.; Lajoie, G. A. J. Am. Chem. Soc. 1993, 115, 5021-5030;
18. (d) Shiokawa, S.; Ohta, T.; Nozoe, S. Chem. Pharm. Bull. 1992, 40, 1398-1399;
19. (e) Roemmele, R. C.; Rapoport, H. J. Org. Chem. 1989, 54, 1866-1875;
20. (f) Takahata, H.; Takamatsu, T.; Yamazaki, T. J. Org. Chem. 1989, 54, 4812-4822;
21. (g) Kunieda, T.; Ishizuka, T.; Higuchi, T.; Hirobe, M. J. Org. Chem. 1988, 53, 3381-3383;
22. (h) Garner, P. Tetrahedron Lett. 1984, 25, 5855-5858.
23. Louwrier, S.; Ostendorf, M.; Boom, A.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1996, 52, 2603-2628.
24. Thaning, M.; Wistrand, L.-G. Acta Chem. Scand. 1989, 43, 290-295.