Electrochemical cyclization of dipeptides to form novel bicyclic, reverse-turn peptidomimetics. 2. Synthesis and conformational analysis of 6,5-bicyclic systems

Journal of Organic Chemistry

Volumn 61, Issue 4, 1996, Pages 1198-1204

  Slomezynska, Urszula ^a,b   Chalmers, David K ^a   Cornille, Fabrice ^a,c   Smythe, Mark L ^a,d   Beusen, Denise D ^a   Moeller, Kevin D ^a   Marshall, Garland R ^a  

^a WASHINGTON UNIVERSITY   (United States)

^b LODZ UNIVERSITY OF TECHNOLOGY   (Poland)

^c INSERM   (France)

^d UNIVERSITY OF QUEENSLAND   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

1 AZA 5 OXA 2 OXOBICYCLI[4 3 0]DECANE DERIVATIVE; BICYCLO COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; ELECTROCHEMISTRY; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0029866877     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo950898o     Document Type: Article

References (51)

1. Cornille, F.; Fobian, Y. M.; Slomczynska, U.; Beusen, D. D.; Marshall, G. R.; Moeller, K. D. Tetrahedron Lett. 1994, 35, 6989-92.
2. Cornille, F.; Slomczynska, U.; Smythe, M. L.; Beusen, D. D.; Moeller, K. D.; Marshall, G. R. J. Am. Chem. Soc 1994, 117. 909-917.
3. Moeller, K. D.; Rutledge, L. D. J. Org. Chem. 1992, 57, 6360-6363.
4. Moeller, K. D.; Wong, P. L. Biomed. Chem. Lett. 1992, 2, 739-742.
5. Moeller, K. D.; Hanau, C. E.; d'Avignon, A. Tetrahedron Lett. 1994, 35, 825.
6. Genin, M. J.; Misra, R. K.; Johnson, R. L. J. Med Chem. 1993, 36, 3481-3483.
7. Genin, M. J.; Johnson, R. L. J. Am. Chem. Soc. 1992,114, 8778-8783.
8. Ripka, W. C.; Lucca, G. V.; Bach, A. C., II; Pottorf, R. S.; Blaney, J. M. Tetrahedron 1993, 49, 3609-3628.
9. Ripka, W. C.; DeLucca, G. V.; Bach, A. C., II; Pottorf, R. S.; Blaney, J. M. Tetrahedron 1993, 49, 3593-3608.
10. Ward, P.; Ewan, G. B.; Jordan, C. C.; Ireland, S. J.; Hagan, R. M.; Brown, J. R. J. Med. Chem. 1990, 33, 1848-1851.
11. Lombart, H.-G.; Lubell, W. D. J. Org. Chem. 1944, 59, 5147-6149.
12. Sato, K.; Hotta, M.; Dong, M.-H.; Hu, H.-Y.; Taulene, J. P.; Goodman, M.; Nagai, U.; Ling, N. Int. J. Pept. Protein Res. 1991, 38, 340-345.
13. Chen, S.; Chrusciel, R. A.; Nakanishi, H.; Raktabutr, A.; Johnson, M. E.; Sato, A.; Weiner, D.; Hoxie, J.; Saragovi, H. U.; Greene, M. I.; Kahn, M. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 5872-5876.
14. Nagai, U.; Sato, K.; Nakamura, R.; Kato, R. Tetrahedron Lett. 1993, 49, 3577-3592.
15. Nagai, U.; Sato, K. Tetrahedron Lett. 1985, 26, 647-650.
16. Baldwin, J. E.; Hulme, C.; Schofield, C. J.; Edwards, A. J. J. Chem. Soc., Chem. Commun. 1993, 935-936.
17. Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367-4416.
18. Shono, T.; Matsumura, Y.; Inoue, K. J. Org. Chem. 1983, 48, 1388-1389.
19. Shono, T.; Matsumura, Y.; Uchida, K.; Tagami, K. Chem. Lett. 1987, 919-922.
20. Thaning, M.; Wistrand, L.-G. Helv. Chim. Acta 1986, 69, 1711.
21. Renaud, P.; Seebach, D. Helv. Chim. Acta 1986, 69, 1704.
22. Renaud, P.; Seebach, D. Angew. Chem., Int. Ed. Engl. 1986, 25, 843.
23. Seebach, D.; Charchuk, R.; Gerber, C.; Renaud, P.; Berner, H.; Schneider, H. Helv. Chim. Acta 1989, 72, 401.
24. Papadopoulos, A.; Heyer, J.; Ginzel, K.-D.; Steckhan, E. Chem. Ber. 1989, 122, 2159.
25. Papadopoulos, A.; Lewall, B.; Steckhan, E.; Ginzel, K.-D.; Knoch, F.; Nieger, M. Tetrahedron 1991, 47, 563.
26. Barrett, A. G. M.; Pilipauskas, D. J. Org. Chem. 1991, 56, 2787-2800.
27. Shono, T. Tetrahedron 1984, 40, 811-850.
28. Ginzel, K-D.; Brungs, P.; Steekhan, E. Tetrahedron Lett. 1989, 45, 1691-1701.
29. Irie, K.; Ban, Y. Heterocycles 1981, 15, 201-206.
30. Irie, K.; Ban, Y. Heterocycles 1982, 18, 255-258.
31. Okita, M.; Wakamatsu, T.; Mori, M.; Ban, Y. Heterocycles 1980, 14, 1089-1092.
32. Okita, M.; Wakamatsu, T.; Ban, Y. Heterocycles 1983, 20, 401-404.
33. Mori, M.; Kagechika, K.; Tohjima, K.; Shibasaki, M. Tetrahedron Lett. 1988, 29, 1409-1412.
34. Magnus, P.; Hulme, C. Tetrahedron Lett. 1994, 35, 8097-8100.
35. Katoh, T.; Nagata, Y.; Kobayashi, Y.; Arai, K.; Minami, J.; Terashima, S. Tetrahedron Lett. 1993, 34, 5743-5746.
36. Slomczynska, U., in preparation.
37. Marfey, P. Carlsberg Res. Commun. 1984, 49, 591.
38. Foster, M. R.; Hornby, E. J.; Brown, S.; Kitchin, J.; Hann, M.; Ward, P. Thromb. Res. 1993, 72, 231-245.
39. Chalmers, D. K.; Marshall, G. R. J. Am. Chem. Soc. 1995, 117, 5927-5937.
40. Ball, J. B.; Alewood, P. F. J. Mol. Recog. 1990, 3, 55-64.
41. Ball, J. B.; Hughes, R. A.; Alewood, P. F.; Andrews, P. R. Tetrahedron 1993, 49, 3467-3478.
42. Bodanszky, M,; Bodanszky, A. The Practice of Peptide Synthesis, 2nd ed.; Springer-Verlag: Berlin, 1994; Vol. 21, p 125.
43. Bernady, K. F.; Floyd, M. B.; Ploetto, J. F.; Weiss, M. J. J. Org. Chem. 1979, 44, 1438.
44. Stork, G.; Takahashi, T.; Kawamoto, L; Suzuki, I. J. Am. Chem. Soc. 1978, 100, 8272-8273.
45. Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440-467.
46. Weiner, S. J.; Kollman, P. A.; Nguyen, D. T.; Case, D. A. J. Comput. Chem. 1986, 7, 230-252.
47. Still, W. C.; Tempczyk, A.; Hawley, R. C.; Hendrickson, T, J. Am. Chem. Soc. 1990, 112, 6127-6129.
48. Goodman, J. M.; Still, W. C. J. Comput. Chem. 1991, 12, 1110-1117.
49. Ponder, J. W.; Richards, F. M. J. Comput. Chem. 1987, 8, 1016-1024.
50. Ryckaert, J.-P.; Ciccotti, G.; Berendsen, H. J. C. J. Comput. Phys. 1977, 23, 327-341.
51. IUPAC-IUB commission on biochemical nomenclature. Biochem. 1970, 9, 3471-3479.