Synthesis of fused heteroarylprolines and pyrrolopyrroles

Journal of Organic Chemistry

Volumn 69, Issue 14, 2004, Pages 4656-4662

  Jeannotte, Guillaume ^a   Lubell, William D ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; CATALYSIS; HYDROGENATION; NITROGEN; OXIDATION;

PEPTIDES; PYRROLOPYRROLES; WACKER OXIDATION;

ESTERS;

1 BENZYL 2 METHYL 1,5 DIHYDROPYRROLO[3,4 B]PYRROLE 4 CARBOXYLIC ACID BENZYL ESTER; 1 N BENZYL 2 METHYL 5 [9 (9 PHENYLFLUORENYL)] 1,4,5,6 TETRAHYDROPYRROLO[3,4 B]PYRROLE 4 CARBOXYLIC ACID BENZYL ESTER; 1 N BUTOXYCARBONYL 2 (2 METHYLTHIOETHYL) 5 [9 (9 PHENYLFLUORENYL)] 1,4,5,6 TETRAHYDROPYRROLO[3,4 B]PYRROLE 4 CARBOXYLIC ACID BENZYL ESTER; 1 N BUTOXYCARBONYL 2 BENZYL 5 [9 (9 PHENYLFLUORENYL)] 1,4,5,6 TETRAHYDROPYRROLO[3,4 B]PYRROLE 4 CARBOXYLIC ACID BENZYL ESTER; 1 N BUTOXYCARBONYL 2 ISOPROPYL 5 [9 (9 PHENYLFLUORENYL)] 1,4,5,6 TETRAHYDROPYRROLO[3,4 B]PYRROLE 4 CARBOXYLIC ACID BENZYL ESTER; 1 N BUTOXYCARBONYL 2 METHYL 5 [9 (9 PHENYLFLUORENYL)] 1,4,5,6 TETRAHYDROPYRROLO[3,4 B]PYRROLE 4 CARBOXYLIC ACID BENZYL ESTER; 1 N BUTOXYCARBONYL 5 [9 (9 PHENYLFLUORENYL)] 1,4,5,6 TETRAHYDROPYRROLO[3,4 B]PYRROLE 4 CARBOXYLIC ACID BENZYL ESTER; 4 OXO 3 (2' OXOPROPYL) 1 [9 (9 PHENYLFLUORENYL)]PROLINE BENZYL ESTER; 4 OXO N 9 (9 PHENYLFLUORENYL)PROLINE BENZYL ESTER; AMINOALDEHYDE; BENZYL DERIVATIVE; DIPEPTIDE; FLUORENE DERIVATIVE; GLYCINE; PHENYLALANINE; PROLINE DERIVATIVE; PYRROLE DERIVATIVE; PYRROLOPYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ALDOL REACTION; ALKYLATION; ALLYLATION; ARTICLE; CATALYST; CYCLIZATION; DIASTEREOISOMER; ENANTIOMER; OXIDATION; PEPTIDE SYNTHESIS; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

COMBINATORIAL CHEMISTRY TECHNIQUES; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PHENYLALANINE; PROLINE; PYRROLES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 3042784692     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049612i     Document Type: Article

References (33)

1. Wagaw, S.; Rennels, R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 8451-8458.
2. Kuwano, R.; Sato, K.; Kurokawa, T.; Karube, D.; Ito, Y. J. Am. Chem. Soc. 2000, 122, 7614-7615.
3. Viswanathan, R.; Prabhakaran, E. N.; Plotkin, M. A.; Johnston, J. N. J. Am. Chem. Soc. 2003, 125, 163-168.
4. Ramos Tombo, G. M.; Schär, H.-P.; Ghisalba, O. Agric. Biol. Chem. 1987, 51, 1833-1838.
5. Kim, D. H.; Guinosso, C. J.; Buzby, G. C. J.; Herbst, D. R.; McCaully, R. J.; Wicks, T. C.; Wendt, R. L. J. Med. Chem. 1983, 26, 394-403.
6. Stanton, J. L.; Gruenfeld, N.; Babiarz, J. E.; Ackerman, M. H.; Friedmann, R. C.; Yuan, A. M.; Macchia, W. J. Med. Chem. 1983, 26, 1267-1277.
7. Gruenfeld, N.; Stanton, J. L.; Yuan, A. M.; Ebetino, F. H.; Browne, L. J.; Gude, C.; Huebner, C. F. J. Med. Chem. 1983, 26, 1277-1282.
8. Cignarella, G.; Cerri, R.; Grella, G.; Sanna, P. Gazz. Chim. Ital. 1976, 106, 65-75.
9. Austin, K. W. B.; Marshall, A. C.; Smith, H. Nature 1985, 208, 999-1000.
10. Long, A. A. W.; Nayler, J. H. C.; Smith, H.; Taylor, T.; Ward, N. J. Chem. Soc. C 1971, 1920-1922.
11. Couture, A.; Deniau, E.; Ioneseu, D.; Grandclaudon, P. Tetrahedron Lett. 1998, 39, 2319-2320.
12. Beeley, L. J.; Rockell, C. J. M. Tetrahedron Lett. 1990, 31, 417-420.
13. Gaertzen, O.; Buchwald, S. L. J. Org. Chem. 2002, 67, 465-475.
14. Gill, P.; Lubell, W. D. J. Org. Chem. 1995, 60, 2658-2659.
15. Rondeau, D.; Gill, P.; Chan, M.; Curry, K.; Lubell, W. D. Bioorg. Med. Chem. Lett. 2000, 10, 771-773.
16. Paal, C. Chem. Ber. 1884, 17, 2756.
17. Knorr, L. Chem. Ber. 1884, 17, 2863.
18. Sharma, R.; Lubell, W. D. J. Org. Chem. 1996, 61, 202-209.
19. Tsuji, J. Synthesis 1984, 369-384.
20. Marcotte, F.-A.; Lubell, W. D. Org. Lett. 2002, 4, 2601-2603.
21. Sha, C.-K.; Liu, J.-M.; Chiang, R.-K.; Wang, S.-U. Heterocycles 1990, 31, 603-609.
22. Gutman, I.; Milun, M.; Trinajstić, N. J. Am. Chem. Soc. 1977, 99, 1692-1704.
23. +) 584.2464, found 584.2487.
24. Nagafuji, P.; Cushman, M. J. Org. Chem. 1996, 61, 4999-5003.
25. Fehrentz, J.-A.; Castro, B. Synthesis 1983, 676-678.
26. Dueholm, K. L.; Egholm, M.; Buchardt, O. Org. Prep. Proc. Int. 1993, 25, 457-461.
27. Blanco, M.-J.; Paleo, M. R.; Penide, C.; Sardina, F. J. J. Org. Chem. 1999, 64, 8786-8793.
28. +) 406.1681, found 406.1652.
29. Rawal, V. H.; Cava, M. P. Tetrahedron Lett. 1985, 26, 6141-6142.
30. Heaney, H.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1973, 499-500.
31. Beausoleil, E.; Sharma, R.; Michnick, S. W.; Lubell, W. D. J. Org. Chem. 1998, 63, 6572-6578.
32. +) 393.1603, found 393.1589.
33. +) 357.2026, found 357.1992.