Expeditious access to unprotected racemic pyroglutamic acids

Journal of Organic Chemistry

Volumn 72, Issue 10, 2007, Pages 3913-3916

  Isaacson, Jerry ^a   Gilley, Cynthia B ^a   Kobayashi, Yoshihisa ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIUM COMPOUNDS; PHENOLS; SYNTHESIS (CHEMICAL);

AMMONIUM ACETATE; INDOLE; KETOACIDS; PYROGLUTAMIC ACIDS;

ORGANIC CARBON;

AMMONIUM ACETATE; INDOLE DERIVATIVE; ISONITRILE DERIVATIVE; OXOACID; PYROGLUTAMIC ACID;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CRYSTALLIZATION; DEPROTECTION REACTION; RACEMIZATION; SYNTHESIS;

AMINES; ANILIDES; INDOLES; METHYLATION; MOLECULAR STRUCTURE; NITRILES; PYRROLIDONECARBOXYLIC ACID; STEREOISOMERISM;

EID: 34248580122     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0700225     Document Type: Article

References (29)

1. (a) Omura, S.; Fujimoto, T.; Otoguro, K.; Matsuzaki, K.; Moriguchi, R.; Tanaka, H.; Sasaki, Y. J. Antibiot. 1991, 44, 113-116.
2. (b) Omura, S.; Matsuzaki, K.; Fujimoto, T.; Kosuge, K.; Furuya, T.; Fujita, S.; Nakagawa, A. J. Antibiot. 1991, 44, 117-118.
3. Feling, R. H.; Buchanan, G. O.; Mincer, T. J.; Kauffman, C. A.; Jensen, P. R.; Fenical, W. Angew. Chem., Int. Ed. 2003, 42, 355-357.
4. Sakai, R.; Oiwa, C.; Takaishi, K.; Kamiya, H.; Tagawa, M. Tetrahedron Lett. 1999, 40, 6941-6944.
5. Mori, T.; Takahashi, K.; Kashiwabara, M.; Uemura, D.; Katayama, C.; Iwadare, S.; Shizuri, Y.; Mitomo, R.; Nakano, F.; Matsuzaki, A. Tetrahedron Lett. 1985, 26, 1073-1076.
6. Nájera, C.; Yus, M. Tetrahedron: Asymmetry 1999, 10, 2245-2303.
7. For a comprehensive review of the Ugi reaction: Ugi, I.; Dömling, A. Angew. Chem., Int. Ed. 2000, 39, 3168-3210.
8. (a) Short, K. M.; Mjalli, A. M. M. Tetrahedron Lett. 1997, 38, 359-362.
9. (b) Harriman, G. C. B. Tetrahedron Lett. 1997, 38, 5591-5594.
10. (c) Hanusch-Kompa, C.; Ugi, I. Tetrahedron Lett. 1998, 39, 2725-2728.
11. (d) Tye, H.; Whittaker, M. Org. Biomol. Chem. 2004, 2, 813-815.
12. Indole-isonitrile (1) was named after the facilitation of hydrolysis of the resulting 2-(2,2-dimethoxyethyl)anilide 3 by Ugi/(Passerini) multicomponent condensation reaction, via N-acylindole 4. The first demonstration of the utility as a convertible isonitrile in the Ugi reaction and its application to natural product synthesis were reported from our laboratory: Gilley, C. B.; Buller, M. J.; Kobayashi, Y. Angew. Chem., Int. Ed. Submitted for publication.
13. Corey, E. J.; Li, W.; Nagamitsu, T. Angew. Chem., Int. Ed. 1998, 37, 1676-1679.
14. Polyakov, A. J.; Aseeva, V. G.; Bezrukova, V. G. Izv. Akad. Nauk SSSR Ser. Khim. 1974, 7, 1597.
15. (a) Kazmaier, U.; Hebach, C. Synlett 2003, 11, 1591-1594.
16. (b) Pick, R.; Bauer, M.; Kazmaier, U.; Hebach, C. Synlett 2005, 5, 757-760.
17. (a) Takenishi, T.; Simamura, O. Bull. Chem. Soc. Jpn. 1954, 27, 207-209.
18. (b) Pfister, K., III; Leanza, W. J.; Conbere, J. P.; Becker, H. J.; Matzuk, A. R.; Rogers, E. F. J. Am. Chem. Soc. 1955, 77, 697-700.
19. Application of indole-isonitrile (1) to Passerini reaction, see: Vamos, M.; Ozboya, K.; Kobayashi, Y. Synlett. Submitted for publication.
20. For previous preparations of 5, see ref 12.
21. For previous preparations of 5a: (a) Gillan, T.; Mor, G.; Pepper, F. W.; Cohen, S. G. Bioorg. Chem. 1977, 6, 329-342.
22. (b) Mkhairi, A.; Hamelin, J. Tetrahedron Lett. 1986, 27, 4435-4436.
23. Clive, D. L. J.; Wang, J. J. Org. Chem. 2004, 69, 2773-2784.
24. Battah, S. H.; Chee, C-E.; Nakanishi, H.; Gerscher, S.; MacRobert, A. J.; Edwards, C. Bioconj. Chem. 2001, 12, 980-988.
25. MacDonald, S. F. Can. J. Chem. 1974, 52, 3257-3258.
26. (a) Newman, M. S.; Beal, P. F., III J. Am. Chem. Soc. 1950, 72, 5161-5163.
27. (b) Marugán, J.; Anaclerio, B.; Lafrance, L.; Lu, T.; Markotan, T.; Leonard, K. A.; Crysler, C.; Eisennagel, S.; Dasgupta, M.; Tomczuk, B. J. Med. Chem. 2005, 48, 926-934.
28. The corresponding ethyl ester of 6c was prepared previously: Guillena, G.; Mico, I.; Najera, C.; Ezquerra, J.; Pedregal, C. An. Quim. Int. Ed. 1996, 92, 362-369.
29. For previous preparations of 10c: Overberger, C. G.; Shalati, M. D. Eur. Polym. J. 1983, 19, 1055-1065.