Diastereoselective syntheses of (2R,3R,5R)- and (2S,3S,5S)-3-hydroxy-5- methyl-2-pyrrolidinecarboxylic acid as a component of actinomycin Z1

Tetrahedron

Volumn 54, Issue 34, 1998, Pages 10029-10042

  Tanaka, Ken Ichi ^a   Sawanishi, Hiroyuki ^a  

^a HOKURIKU UNIVERSITY   (Japan)

Author keywords

Asymmetric synthesis; Lactam synthesis; N Acyliminium ion; Stereoselection; Unusual amino acids

Indexed keywords

3 HYDROXY 5 METHYL 2 PYRROLIDINECARBOXYLIC ACID; ACTINOMYCIN DERIVATIVE; ACTINOMYCIN Z1; CARBOXYLIC ACID DERIVATIVE; CYANIDE; UNCLASSIFIED DRUG;

ARTICLE; DIASTEREOISOMER; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; PRIORITY JOURNAL; STEREOCHEMISTRY; STREPTOMYCES FRADIAE; STRUCTURE ANALYSIS;

STREPTOMYCES FRADIAE;

EID: 0032552178     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00604-8     Document Type: Article

References (24)

1. 1. Katz, E.; Mason, K. T.; Mauger, A, B. Biochem. Biophys. Res. Commun. 1975, 63, 502-508.
2. 2. Mauger, A. B.; Stuart, O. A.; Katz, E.; Mason, K. T. J. Org. Chem. 1977, 42, 1000-1005.
3. 3. Fushiya, S.; Chiba, H.; Otsubo, A.; Nozoe, S. Chem. Lett. 1987, 2229-2232.
4. 4. a) Tanaka, K.; Sawanishi, H. Tetrahedron: Asymmetry 1995, 6, 1641-1656.
5. b) Tanaka, K.; Iwabuchi, H.; Sawanishi, H. Tetrahedron: Asymmetry 1995, 6, 2271-2279.
6. c) Tanaka, K.; Suzuki, H.; Sawanishi, H. Heterocycles 1996, 43, 205-219.
7. 5. a) Thaning, M.; Wistrand, L-G. Acta. Chem. Scad. 1989, 43, 290-295.
8. b) Corey, E. J.; Yuen, P. W.; Hannon, F. J.; Wierda, D. A. J. Org. Chem. 1990, 55, 784-786.
9. c) Langlois, N.; Rojas, A. Tetrahedron 1993, 49, 77-82.
10. d) Katoh, T.; Nagata, Y.; Kobayashi, Y.; Arai, K.; Minami, J.; Terashima, S. Tetrahedron 1994, 50, 6221-6238.
11. e) Cotton, R.; Johnstone, A. N. C.; North, M. Tetrahedron 1995, 51, 8525-8544.
12. f) Langlois, N.; R-Rousseau, A.; Decavallas, O. Tetrahedron: Asymmetry 1996, 7, 1095-1100.
13. g) Panday, S-K.; Langlois, N. Synth. Commun. 1997, 27, 1373-1384.
14. 6. a) Shono, T.; Fujita, T.; Matsumura, Y. Chem. Lett. 1991, 81-84.
15. b) Matsumura, Y.; Tomita, T. Tetrahedron Lett. 1994, 35, 3737-3740.
16. 7. Tanaka, K.; Sawanishi, H. Tetrahedron: Asymmetry 1998, 9, 71-77.
17. 8. Rosen, T.; Chu, D. T. W.; Lico, I. M.; Fernandes, P. B.; Marsh, K.; Shen, L.; Cepa, V. G.; Pernet, A. G. J. Med. Chem. 1988, 31, 1598-1611.
18. 9. Li, H.; Sakamoto, T.; Kato, M.; Kikugawa, Y. Synth. Commun. 1995, 25, 4045-4052.
19. 10. a) Kozikowski, A. P.; Sorgi, K. L.; Tetrahedron Lett. 1982, 23, 2281-2284.
20. b) Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976-4978.
21. c) Thaning, M.; Wistrand, L. G. Helv. Chim. Acta. 1986, 69, 1711-1717.
22. 11. Stevens, R. V. Acc. Chem. Res. 1984, 17, 289.
23. 12. Williams, M. A.; Rapoport, H. J. Org. Chem. 1994, 59, 3616-3625 and references cited therein.
24. 13. Mitsunobu, O. Synthesis 1981, 1-28.