Synthesis of physiologically potent β-amino alcohols

Synlett

Volumn , Issue 10, 2004, Pages 1673-1685

  Lee, Hee Seung ^a,b,c,d   Kang, Sung Ho ^a,b,e,f,g,h  

^a Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

^b KAIST ^*

^c Samsung Fine Chemicals Co   (South Korea)

^d UNIVERSITY OF WISCONSIN MADISON   (United States)

^e Seoul National University   (South Korea)

^f UNIVERSITY OF TEXAS AT AUSTIN   (United States)

^g HARVARD UNIVERSITY   (United States)

^h Department of Chemistry   (South Korea)

Author keywords

Electrophile promoted; Intramolecular animation; Natural products; Trichloroacetimidate; amino alcohols

Indexed keywords

ALCOHOL DERIVATIVE; ALKENE DERIVATIVE; ANISOMYCIN; ANTIBIOTIC AGENT; CARBAPENEM; CARBOHYDRATE DERIVATIVE; CASTANOSPERMINE; CHLORINE DERIVATIVE; FURANOMYCIN; N ACETYLNEURAMINIC ACID; OXAMIC ACID; STATIN; UNCLASSIFIED DRUG;

AMINATION; DRUG STRUCTURE; DRUG SYNTHESIS; MOLECULAR DYNAMICS; REVIEW; STEREOCHEMISTRY;

EID: 4143050267     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-829578     Document Type: Review

References (53)

1. Bergmeier, S. C. Tetrahedron 2000, 56, 2561.
2. Kempf, D. J.; Sowin, T. J.; Doherty, E. M.; Hannick, S. M.; Codavoci, L.; Henry, R. F.; Green, B. E.; Spanton, S. G.; Norbeck, D. W. J. Org. Chem. 1992, 57, 5692.
3. Chan, M. F.; Hsiao, C. N. Tetrahedron Lett. 1992, 33, 3567.
4. Baker, W. R.; Condon, S. L. J. Org. Chem. 1993, 58, 3277.
5. Elbein, A. D. FASEB 1991, 5, 3055.
6. Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835.
7. Reetz, M. T. Chem. Rev. 1999, 99, 1121.
8. Paleo, M. R.; Calaza, M. I.; Sardina, F. J. J. Org. Chem. 1997, 62, 6862.
9. Sasai, H.; Itoh, N.; Suzuki, T.; Shibasaki, M. Tetrahedron Lett. 1993, 34, 7693.
10. Fisher, G. B.; Goralski, C. T.; Nicholson, L. W.; Hasha, D. L.; Zakett, D.; Singaram, B. J. Org. Chem. 1995, 60, 2026.
11. Castejon, P.; Moyano, A.; Pericas, M. A.; Riera, A. Tetrahedron 1996, 52, 7063.
12. Bongini, A.; Cardillo, G.; Orena, M.; Sandri, S.; Tomasini, C. J. Org. Chem. 1986, 51, 4905.
13. For a review see: (a) Cardillo, G.; Orena, M. Tetrahedron 1990, 46, 3321. (b) Orena, M. In Houben-Weyl, Methods of Organic Chemistry, Stereoselective Synthesis, Vol. E 21e; Thieme: Stuttgart, 1996, 5291-5355.
14. For a review see: (a) Cardillo, G.; Orena, M. Tetrahedron 1990, 46, 3321. (b) Orena, M. In Houben-Weyl, Methods of Organic Chemistry, Stereoselective Synthesis, Vol. E 21e; Thieme: Stuttgart, 1996, 5291-5355.
15. Chamberlin, A. R.; Mulholland, R. L. Jr.; Kahn, S. D.; Hehre, W. J. J. Am. Chem. Soc. 1987, 109, 672.
16. Elbein, A. D.; Molyneux, R. J. Alkaloids: Chemical and Biological Perspectives, Vol. 5; Pelletier, S. W., Ed.; Wiley-Interscience: New York, 1987, 1.
17. Kang, S. H.; Kim, G. T. Tetrahedron Lett. 1995, 36, 5049.
18. Kang, S. H.; Kim, J. S.; Youn, J.-H. Tetrahedron Lett. 1998, 39, 9047.
19. Kang, S. H.; Kim, J. S. Chem. Commun. 1998, 1353.
20. Kang, S. H.; Choi, H.-W.; Kim, J. S.; Youn, J.-H. Chem. Commun. 2000, 227.
21. Cha, J. K.; Christ, W. J.; Kishi, Y. Tetrahedron Lett. 1983, 24, 3943.
22. Shih, D. H.; Baker, F.; Cama, L.; Christensen, B. G. Heterocycles 1984, 21, 29.
23. Kang, S. H.; Kim, M.; Ryu, D. H. Synlett 2003, 1149.
24. Kaga, H.; Kobayashi, S.; Ohno, M. Tetrahedron Lett. 1989, 30, 113.
25. Kang, S. H.; Ryu, D. H. Bull. Korean Chem. Soc. 1996, 17, 219.
26. Umezawa, H.; Aoyagi, T.; Morishima, H.; Matsuzaki, M.; Hamada, M.; Takeuchi, T. J. Antibiot. 1970, 23, 259.
27. Kang, S. H.; Ryu, D. H. Bioorg. Med. Chem. Lett. 1995, 5, 2959.
28. Nebois, P.; Greene, A. E. J. Org. Chem. 1996, 61, 5210.
29. Rich, D. H.; Moon, B. J.; Boparai, A. S. J. Org. Chem. 1980, 45, 2288.
30. Iizuka, K.; Kamijo, T.; Kubota, T.; Akahane, K.; Umeyama, H.; Kiso, Y. J. Med. Chem. 1988, 31, 701.
31. Pasto, M.; Castejon, P.; Moyano, A.; Pericas, M. A.; Riera, A. J. Org. Chem. 1996, 61, 6033.
32. Suda, H.; Takita, T.; Aoyagi, T.; Uemezawa, H. J. Antibiot. 1976, 29, 100.
33. Righi, G.; D'Achille, C.; Pescatore, G.; Bonini, C. Tetrahedron Lett. 2003, 44, 6999.
34. Grollman, A. P.; Walsh, M. J. Biol. Chem. 1967, 242, 3226.
35. Schwardt, O.; Veith, U.; Gaspard, C.; Jager, V. Synthesis 1999, 1473.
36. Savage, I.; Thomas, E. J. J. Chem. Soc., Chem. Commun. 1989, 717.
37. Kang, S. H.; Choi, H.-w. Chem. Commun. 1996, 1521.
38. Katagiri, K.; Tori, K.; Kimura, Y.; Yoshida, T.; Nagasaki, T.; Minato, H. J. Med. Chem. 1967, 10, 1149.
39. Kohno, T.; Kohda, D.; Haruki, M.; Yokoyama, S.; Miyazawa, T. J. Biol. Chem. 1990, 265, 6931.
40. Parry, R. J.; Buu, H. P. J. Am. Chem. Soc. 1983, 105, 7446.
41. Parry, R. J.; Turakhia, R.; Buu Hanh, P. J. Am. Chem. Soc. 1988, 110, 4035.
42. Kang, S. H.; Lee, S. B. Chem. Commun. 1998, 761.
43. Kang, S. H.; Ryu, D. H. Chem. Commun. 1996, 355.
44. Kang, S. H.; Ryu, D. H. Tetrahedron Lett. 1997, 38, 607.
45. Kang, S. H.; Hwang, Y. S.; Youn, J. H. Tetrahedron Lett. 2001, 42, 7599.
46. Kang, S. H.; Hwang, Y. S.; Lee, H. S. Bull. Korean Chem. Soc. 2002, 23, 1195.
47. Kang, S. H.; Kim, G. T.; Yoo, Y. S. Tetrahedron Lett. 1997, 38, 603.
48. Omura, S.; Fujimoto, T.; Otoguro, K.; Matsuzaki, K.; Moriguchi, R.; Tanaka, H.; Sasaki, Y. J. Antibiot. 1991, 44, 113.
49. Kang, S. H.; Jun, H.-S.; Youn, J.-H. Synlett 1998, 1045.
50. Roush, W. R.; Ando, K.; Powers, D. B.; Palkowitz, A. D.; Halterman, R. L. J. Am. Chem. Soc. 1990, 112, 6339.
51. Uno, H.; Baldwin, J. E.; Russell, A. T. J. Am. Chem. Soc. 1994, 116, 2139.
52. Kang, S. H.; Kim, C. M.; Youn, J.-H. Tetrahedron Lett. 1999, 40, 3581.
53. Kingston, D. G. I.; Chaudhary, A. G.; Gunatilaka, A. A. L.; Middleton, M. L. Tetrahedron Lett. 1994, 35, 4483.