Isolation and synthesis of (-)-(5S)-2-Imino-1-methylpyrrolidine-5- carboxylic acid from cliona tenuis: Structure revision of pyrostatins

Organic Letters

Volumn 8, Issue 21, 2006, Pages 4967-4970

  Castellanos, Leonardo ^a   Duque, Carmenza ^a   Zea, Sven ^b   Espada, Alfonso ^c   Rodríguez, Jaime ^d   Jiménez, Carlos ^d  

^a UNIVERSIDAD NACIONAL DE COLOMBIA   (Colombia)

^b Instituto de Investigaciones Marinas   (Colombia)

^c ELI LILLY AND COMPANY   (Spain)

^d UNIVERSITY OF A CORUÑA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

DIAMINO ACID; ECTOINE; HYDROXYECTOINE; IMINE; PYROSTATIN A; PYROSTATIN B; PYRROLIDINE DERIVATIVE;

ANIMAL; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ISOLATION AND PURIFICATION; NUCLEAR MAGNETIC RESONANCE; SPONGE (PORIFERA); STEREOISOMERISM; SYNTHESIS;

AMINO ACIDS, DIAMINO; ANIMALS; IMINES; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PORIFERA; PYRROLIDINES; STEREOISOMERISM;

EID: 33750356992     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062087k     Document Type: Article

References (29)

1. O'Hagan, D. Nat. Prod. Rep. 2000, 17, 435-446.
2. Mitchell, R. E.; Teh, K. L. Org. Biomol. Chem. 2005, 3, 3540-3543.
3. (a) Hagen, T. J.; Bergmanis, A. A.; Kramer, S. W.; Fok, K. F.; Schmelzer, A. E.; Pitzele, B. S.; Swenton, L.; Jerome, G. M.; Kornmeier, G. M.; Moore, W. M.; Branson, L. F.; Connor, J. R.; Manning, P. T.; Currie, M. G.; Hallinan, E. A. J. Med. Chem. 1998, 41, 3675-3683.
4. (b) Tsymbalov, S.; Hagen, T. J.; Moore, W. M.; Jerome, G. M.; Connor, J. R.; Manning, P. T.; Pitzele, B. S.; Hallinan, E. A. Bioorg. Med. Chem. Lett. 2002, 12, 3337-3339.
5. (c) Benati, L.; Bencivenni, G.; Leardini, R.; Nanni, D.; Minozzi, M.; Spagnolo, P.; Scialpi, R.; Zanardi, G. Org. Lett. 2006, 8, 2499-2502.
6. (a) López-Victoria, M.; Zea, S.; Weil, E. Mar. Ecol. Prog. Ser. 2006, 312, 113-121.
7. (b) Petrichtcheva, N. V.; Duque, C.; Dueñas, A.; Zea, S.; Hara, N.; Fujimoto, Y. J. Nat. Prod. 2002, 65, 851-855.
8. Unpublished results.
9. Fattorusso, E.; Taglialatela-Scafati, O.; Petrucci, F.; Bavestrello, G.; Calcinai, B.; Cerrano, C.; Di Meglio, P.; Ianaro, A. Org. Lett. 2004, 6, 1633-1635.
10. (a) Andersen, R. J. Tetrahedron Lett. 1978, 2541-2544.
11. (b) Andersen, R. J.; Stonard, R. J. Can. J. Chem. 1979, 57, 2325-2338.
12. (c) Stonard, R. J.; Andersen, R. J. J. Org. Chem. 1980, 45, 3687-3691.
13. (d) Stonard, R. J.; Andersen, R. J. Can. J. Chem. 1980, 58, 2121-2126.
14. (e) Palermo, J. A.; Rodríguez, M. F.; Cabezas, E.; Balzaretti, V.; Seldes, A. M. J. Nat. Prod. 1998, 61, 488-490.
15. Palermo, J. A.; Rodríguez, M. F.; Seldes, A. M. Tetrahedron 1996, 52, 2727-2734.
16. (a) Aoyama, T.; Kojima, F.; Imada, C.; Muraoka, Y.; Naganawa, H.; Okami, Y.; Takeuchi, T.; Aoyagi, T. J. Enzyme Inhib. 1995, 8, 223-232.
17. (b) Imada, C. Antonie van Leeuwenhoek 2005, 87, 59-63.
18. Inbar, L.; Lapidot, A. J. Biol. Chem. 1988, 263, 16014-16022.
19. Inbar, L.; Frolow, F.; Lapidot, A. Eur. J. Biochem. 1993, 214, 897-906.
20. Takeuchi, T.; Aoyanagi, T.; Okami, Y.; Osanawa, H.; Muraoka, Y.; Imada, C.; Aoyama, T. Jpn. Kokai Tokkyo Koho 1995, 12 pp. JP 07291924 A2 19951107 Heisei.
21. (a) Rama Rao, K.; Nageswar, Y. V. D.; Srinivasan, T. N.; Sattur, P. B. Synth. Commun. 1988, 18, 877-880.
22. (b) Rama Rao, K.; Nageswar, Y. V. D.; Srinivasan, T. N.; Satur, P. B. Indian J. Chem. 1990, 29B, 1041-1043.
23. (a) Kolasa, T.; Miller, M. J. J. Org. Chem. 1990, 55, 1711-1721.
24. (b) Itoh, T.; Miyazaki, M.; Ikeda, S.; Nagata, K.; Yokoya, M.; Matsuya, Y.; Enomoto, Y.; Ohsawa, A. Tetrahedron 2003, 59, 3527-3536.
25. Winkler, T. Magn. Reson. Chem. 2006, 44, 571-572.
26. Galinski, E. A.; Pfeiffer, H.-P.; Trüper, H. G. Eur. J. Biochem. 1985, 149, 135-139.
27. Sigma (E 2271) and Fluka (81619) catalogues.
28. Woynarowska, B.; Wikiel, H.; Sharma, M.; Carpenter, N.; Fleet, G. W. J.; Bernacki, R. J. Anticancer Res. 1992, 12, 161-166.
29. Muzzarelli, R. A. A. EXS 1999, 87, 235-247 (CAN 132: 104447).