Enantioselective syntheses and biological studies of aeruginosin 298-A and its analogs: Application of catalytic asymmetric phase-transfer reaction

Proceedings of the National Academy of Sciences of the United States of America

Volumn 101, Issue 15, 2004, Pages 5433-5438

  Fukuta, Yuhei ^a   Ohshima, Takashi ^a   Gnanadesikan, Vijay ^a   Shibuguchi, Tomoyuki ^a   Nemoto, Tetsuhiro ^a   Kisugi, Takaya ^b   Okino, Tatsufumi ^b   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AERUGINOSIN 298 A; BACTERIAL PROTEIN; LANTHANIDE; LANTHANIDE BINOL COMPLEX; SERINE PROTEINASE INHIBITOR; THROMBIN; TRYPSIN INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; CYANOBACTERIUM; ENANTIOSELECTIVITY; EPOXIDATION; MICROCYSTIS AERUGINOSA; PHASE TRANSITION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ALKYLATION; CATALYSIS; EPOXY COMPOUNDS; INHIBITORY CONCENTRATION 50; LEUCINE; NAPHTHOLS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TRYPSIN INHIBITORS;

BACTERIA (MICROORGANISMS); MICROCYSTIS; MICROCYSTIS AERUGINOSA;

EID: 1842782786     PISSN: 00278424     EISSN: None     Source Type: Journal    
DOI: 10.1073/pnas.0307154101     Document Type: Article

References (42)

1. Vacca, J. (1998) in Annual Reports in Medicinal Chemistry, ed. Bristol, J. A. (Academic, San Diego), pp. 81-90.
2. Bode, W., Brandstetter, H., Mather, T. & Stubbs, M. T. (1997) Thromb. Haemostasis 78, 501-511.
3. Magill, C., Katz, B. A. & Mackman, R. L. (1999) Emerging Ther. Targets 3, 109-133.
4. Andreasen, P. A., Kjøller, L., Christensen, L. & Duffy, M. J. (1997) Int. J. Cancer 72, 1-22.
5. Rabbani, S. A. & Xing, R. H. (1998) J. Int. Oncol. 12, 911-920.
6. Murakami, M., Okita, Y., Matsuda, H., Okino, T. & Yamaguchi, K. (1994) Tetrahedron Lett. 35, 3129-3132.
7. Ishida, K., Okita, Y., Matsuda, H., Okino, T. & Murakami, M. (1999) Tetrahedron 55, 10971-10988.
8. Matsuda, H., Okino, T., Murakami, M. & Yamaguchi, K. (1996) Tetrahedron 52, 14501-14506.
9. Kodani, S., Ishida, K. & Murakami, M. (1998) J. Nat. Prod. 61, 1046-1048.
10. Banker, S. & Carmeli, S. (1999) Tetrahedron 55, 10835-10844.
11. Valls, N., López-Canet, M., Vallribera, M. & Bonjoch, J. (2000) J. Am. Chem. Soc. 122, 11248-11249.
12. Valls, N., López-Canet, M., Vallribera, M. & Bonjoch, J. (2001) Chem. Eur. J. 7, 3446-3460.
13. Wipf, P. & Methot, J.-L. (2000) Org. Lett. 2, 4213-4216.
14. Shibuguchi, T., Fukuta, Y., Akachi, Y., Sekine, A., Ohshima, T. & Shibasaki, M. (2002) Tetrahedron Lett. 43, 9539-9543.
15. Ohshima, T., Gnanadesikan, V., Shibuguchi, T., Fukuta, Y., Nemoto, T. & Shibasaki, M. (2003) J. Am. Chem. Soc. 125, 11206-11207.
16. Nemoto, T., Ohshima, T., Yamaguchi, K. & Shibasaki, M. (2001) J. Am. Chem. Soc. 123, 2725-2732.
17. Nemoto, T., Ohshima, T. & Shibasaki, M. (2002) J. Synth. Org. Chem. Jpn. 60, 94-105.
18. Nemoto, T., Ohshima, T. & Shibasaki, M. (2001) J. Am. Chem. Soc. 123, 9474-9475.
19. Nemoto, T., Tosaki, S.-y., Ohshima, T. & Shibasaki, M. (2003) Chirality 15, 306-311.
20. Nemoto, T., Kakei, H., Gnanadesikan, V., Tosaki, S.-y., Ohshima, T. & Shibasaki, M. (2002) J. Am. Chem. Soc. 124, 14544-14545.
21. Tosaki, S.-y., Nemoto, T., Ohshima, T. & Shibasaki, M. (2003) Org. Lett. 5, 495-498.
22. Ohshima, T., Nemoto, T., Tosaki, S.-y., Kakei, H., Gnanadesikan, V. & Shibasaki, M. (2003) Tetrahedron 59, 10485-10497.
23. Maruoka, K. & Ooi, T. (2003) Chem. Rev. 103, 3013-3028.
24. O'Donnell, M. J., Bennett, W. D. & Wu, S. (1989) J. Am. Chem. Soc. 111, 2353-2355.
25. Corey, E. J., Xu, F. & Noe, M. C. (1997) J. Am. Chem. Soc. 119, 12414-12415.
26. Lygo, B. & Wainwright, P. G. (1997) Tetrahedron Lett. 38, 8595-8598.
27. Park, H.-g., Jeong, B.-S., Yoo, M.-S., Lee, J.-H., Park, M.-k., Lee, Y.-J., Kim, M.-J. & Jew, S.-s. (2002) Angew. Chem. Int. Ed. Engl. 41, 3036-3038.
28. Ooi, T., Kaneda, M. & Maruoka, K. (1999) J. Am. Chem. Soc. 121, 6519-6520.
29. Belokon, Y. N., Kochetkov, K. A., Churkina, T. D., Ikonnikov, N. S., Larionov, O. V., Harutyunyan, S. R., Vyskocil, S., North, M. & Kagan, H. B. (2001) Angew. Chem. Int. Ed. Engl. 40, 1948-1951.
30. Kita, T., Georgieva, A., Hashimoto, Y., Nakata, T. & Nagasawa, K. (2002) Angew. Chem. Int. Ed. Engl. 41, 2832-2834.
31. Arai, S., Tsuji, R. & Nishida, A. (2002) Tetrahedron Lett. 43, 9535-9537.
32. Mase, N., Ohno, T., Hoshikawa, N., Ohishi, K., Morimoto, H., Yoda, H. & Takabe, K. (2003) Tetrahedron Lett. 44, 4073-4075.
33. Dharmpal, S. D. & Kozikowski, A. P. (1994) Tetrahedron Lett. 35, 977-980.
34. Daikai, M., Kamaura, M. & Inanaga, J. (1998) Tetrahedron Lett. 39, 7321-7322.
35. Daikai, M., Hayano, T., Kino, R., Furuno, H., Kagawa, T. & Inanaga, J. (2003) Chirality 15, 83-88.
36. Trzeciak, A. & Bannwarth, W. (1996) Synthesis 1433-1434.
37. Nigam, S. C., Mann, A., Taddei, M. & Wermuth, C.-G. (1989) Synth. Commun. 19, 3139-3142.
38. Ohshima, T., Xu, Y., Takita, R., Shimizu, S., Zhong, D. & Shibasaki, M. (2002) J. Am. Chem. Soc. 124, 14546-14547.
39. Coste, J., Le-Nguyen, D. & Castro, B. (1990) Tetrahedron Lett. 31, 205-208.
40. Carpino, L. A. (1993) J. Am. Chem. Soc. 115, 4397-4398.
41. Sandler, B., Murakami, M. & Clardy, J. (1998) J. Am. Chem. Soc. 120, 595-596.
42. Jorge, L., Steiner, R., Murakami, M. & Tulinsky, A. (1998) J. Am. Chem. Soc. 120, 597-598.