Synthesis of substituted-(l)-tryptophanols from an enantiomerically pure aziridine-2-methanol

Organic Letters

Volumn 3, Issue 26, 2001, Pages 4197-4199

  Pyun, Do Kyu ^a,b   Lee, Cheol Hae ^a,b   Ha, Hyun Joon ^a,c   Park, Chan Sun ^a   Chang, Jae Won ^a   Lee, Won Koo ^a  

^a Sogang University   (South Korea)

^b Korea Research Institute of Chemical Technology   (South Korea)

^c Hankuk University of Foreign Studies   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001115239     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016861+     Document Type: Article

References (43)

1. Gollnick, P. Mol. Microbiol. 1994, 11, 991.
2. Babitzke, P.; Yanofsky, C. J. Biol. Chem. 1995, 270, 12452.
3. Anderson, M. Science 1945, 101, 565.
4. (a) Ma, C.; Liu, X.; Li, X.; Anderson, J. F.; Yu, S.; Cook, J. M. J. Org. Chem. 2001, 66, 4525.
5. (b) Murray, P. J.; Kranz, M.; Ladlow, M.; Taylor, S.; Berst, F.; Holmes, A. B.; Keavey, K. N.; Albert, J.; Seale, P. W.; Stead, P.; Upton, R. J.; Croft, S. L.; Clegg, W.; Elsegood, M. R. Bioorg. Med. Chem. Lett. 2001, 11, 773.
6. (c) Bailey, P. D.; Collier, I. D.; Hollinshead, S. P.; Moore, M. H.; Morgan, K. M.; Smith, D. I.; Vernon, J. M. J. Chem. Soc., Perkin Trans. 1 1997, 1209.
7. (d) Gellerman, G.; Ruid, A.; Kashman, Y. Tetrahedron 1994, 50, 12959.
8. (e) Kagan, T. P.; Somers, T. C.; Venuri, M. C. Tetrahedron 1990, 46, 6623.
9. (f) Gan, T,; Liu, R.; Yu, P.; Zhao, S.; Cook, J. M. J. Org. Chem. 1997, 62, 9298.
10. (g) Semmelhack, M. F.; Rhee, H. Tetrahedron Lett. 1993, 34, 1395.
11. (a) Shima, I.; Shimazaki, N.; Imai, K.; Hemmi, K.; Hashimoto, M. Chem. Pharm. Bull. 1990, 38, 564.
12. (b) Sato, K.; Kozikowski, A. P. Tetrahedron Lett. 1989, 30, 4073.
13. (c) Bennani, Y. L.; Zhu, G.-D.; Freeman, J. C. Synlett 1998, 754.
14. (a) Yokoyama, Y.; Osanai, K.; Mitsuhashi, M.; Kondo, K.; Murakami, Y. Heterocycles 2001, 55, 653.
15. (b) Nettekoven, M.; Psiorz, M.; Waldmann, H. Tetrahedron Lett. 1995, 36, 1425.
16. (a) Zhang, P.; Cook, J. M. Synth. Commun. 1995, 25, 3883.
17. (b) Zhang, P.; Liu, R.; Cook, J. M. Tetrahedron Lett. 1995, 35, 7411.
18. Cavallo, A. S.; Schwarz, J.; Mouza, C. Tetrahedron Lett. 1998, 39, 3861.
19. (a) Yokoyama, Y.; Kondo, K.; Mitushashi, M.; Murakami, Y., Tetrahedron Lett. 1996, 37, 9309.
20. (b) Osanai, K.; Yokoyama, Y.; Kondo, K.; Murakami, Y. Chem. Pharm. Bull. 1999, 47, 1587.
21. (a) Oddo, B. Chem. Ber. 1910, 43, 1012.
22. (b) Powers, J. C. J. Org. Chem. 1965, 30, 2534.
23. (c) Bader, H.; Onoshnik, W. J. Am. Chem. Soc. 1959, 81, 163.
24. (d) Acheson, R. M.; Hands, A. R. J. Chem. Soc. 1961, 744.
25. (a) Lim, Y.; Lee, W. K. Tetrahedron Lett. 1995, 36, 8431.
26. (b) Hwang, G. I.; Chung, J. H.; Lee, W. K. J. Org. Chem. 1996, 61, 6183
27. Cardillo, G.; Orena, M. Tetrahedron 1990, 46, 3321.
28. Duddu, R.; Eckhardt, E.; Furlong, M.; Knoess, H. P.; Berger, S.; Knochel, P. Tetrahedron Lett. 1994, 50, 2415.
29. (b) Karatens, W. F. J.; Stol, M.; Rutjes, F. J. T.; Hiemstra, H. Synlett 1998, 1126.
30. Bertozzi, C. R.; Hoeprich, P. D.; Bednarski, M. D. J. Org. Chem. 1992, 57, 6092.
31. Sugiyama, S.; Morishita, K.; Ishii, K. Heterocycles 2001, 55, 353.
32. Cardillo, G.; Orena, M.; Sandri, S.; Tomasini, C. Tetrahedron 1987, 43, 2505.
33. Sibi, M. P.; Ji, J. J. Am. Chem. Soc. 1996, 118, 3063.
34. Sibi, M. P.; Harris, B. J.; Shay, J. J.; Hajra, S. Tetrahdron 1998, 54, 7221.
35. DeGraw, J. I.; Kennedy, J. G.; Skinner, W. A. J. Heterocycl. Chem. 1966, 3, 67.
36. (a) Giuliana, C.; Mario, O.; Sergio, S.; Claudia, T. Tetrahedron Lett. 1987, 43, 2505.
37. (b) Cecilia, A. P.; Eusebio, J.; Leticia, Q.; Angel, C.-S. Tetrahedron: Asymmetry 1997, 8, 1075.
38. (a) Madalengoitia, J. S.; Tepe, J. J.; Werbovetz, K. A.; Lehnert, E. K.; Macdonald, T. L. Bioorg. Med. Chem. Lett. 1997, 5, 1807.
39. (b) Tepe, J. J.; Madalengitia, J. S.; Slunt, K. M.; Werbovetz, K. W.; Spoors, P. G.; Macdonald, T. L. J. Med. Chem. 1996, 39, 2188.
40. (c) Cardillo, G.; Gentilucci, L.; Tomasini, C.; Tomasoni, L. Tetrahedron: Asymmetry 1995, 6, 1947.
41. Agani, C.; Amiot, F.; Couty, F.; Dechoux, L.; Kaminsky, C.; Venier, O. Tetrahedron: Asymmetry 1998, 9, 3955
42. Sugiyama, S.; Morishita, K.; Ishii, K. Heterocycles 2001, 55, 353.
43. 3, 200 MHz) δ 8.27(s, 1H), 7.73 (d, J = 11.4 Hz, 1H), 7.36-7.20 (m, 2H), 6.63 (d, J = 8.4 Hz, 1H), 5.68 (s, 1H), 4.20 (m, 1H), 3.84 (m, 1H), 2.95-2.86 (m, 2H).