Concise construction of novel bridged bicyclic lactams by sequenced Ugi/RCM/Heck reactions

Organic Letters

Volumn 9, Issue 24, 2007, Pages 5119-5122

  Ribelin, Timothy P ^a   Judd, Andrew S ^a   Akritopoulou Zanze, Irini ^a   Henry, Rodger F ^a   Cross, Jeffrey L ^a   Whittern, David N ^a   Djuric, Stevan W ^a  

^a ABBOTT LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LACTAM;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; LACTAMS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 36849027181     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol7023373     Document Type: Article

References (29)

1. For a recent review, see: Doemling, A. Chem. Rev. 2006, 106, 17-89.
2. (a) Tempest, P.; Ma, V.; Kelly, M. G.; Jones, W.; Hulme, C. Tetrahedron Lett. 2001, 42, 4963-4968.
3. (b) Hulme, C.; Peng, J.; Morton, G.; Salvino, J. M.; Herpin, T.; Labaudiniere, R. Tetrahedron Lett. 1998, 39, 7227-7230.
4. (c) Strocker, A. M.; Keating, T. A.; Tempest, P. A.; Armstrong, R. W. Tetrahedron Lett. 1996, 37, 1149-1152.
5. (d) Short, K. M.; Ching, B. W.; Mjalle, A. M. M. Tetrahedron Lett. 1996, 37, 7489-7492.
6. (e) Krelaus, R.; Westermann, B. Tetrahedron Lett. 2004, 45, 5987-5990.
7. (a) Akritopoulou-Zanze, I.; Whitehead, A.; Waters, J. E.; Henry, R. F.; Djuric, S. W. Org. Lett. 2007, 9, 1299-1302.
8. (b) Gracias, V.; Moore, J. D.; Djuric, S. W. Tetrahedron Lett. 2004, 45, 417-420.
9. (c) Akritopoulou-Zanze, I.; Gracias, V.; Moore, J. D.; Djuric, S. W. Tetrahedron Lett. 2004, 45, 3421-3423.
10. (d) Akritopoulou-Zanze, I.; Gracias, V.; Djuric, S. W. Tetrahedron Lett. 2004, 45, 8439-8441.
11. (a) Beck, B.; Larbig, G.; Mejat, B.; Magnin-Lachaux, M.; Picard, A.; Herdtweck, E.; Doemling, A. Org. Lett. 2003, 5, 1047-1050.
12. (b) Basso, A.; Banfi, L.; Riva, R.; Guanti, G. Tetrahedron 2006, 62, 8830-8837.
13. (c) El Kaim, L.; Gizolme, M.; Grimaud, L. Synlett 2007, 227-23.
14. Sunderhaus, J. D.; Dockendorff, C.; Martin, S. F. Org. Lett. 2007, 9, 4223-4226.
15. For a review of twisted amides, see: (a) Greenberg, A. Mol. Struct. Energ. 1988, 7, 139-178.
16. For recent reports of twisted amides, see: (a) Tani, K.; Stoltz, B. M. Nature 2006, 441, 731-734.
17. (b) Ly, T.; Krout, M.; Pham, D. K.; Kousuke, T.; Stoltz, B. M.; Julian, R. R. J. Am. Chem. Soc. 2007, 129, 1864-1865.
18. (c) Yao, L.; Aube, J. J. Am. Chem. Soc. 2007, 129, 2766-2767.
19. (d) Bashore, C. G.; Samardjiev, I. J.; Bordner, J.; Coe, J. W. J. Am. Chem. Soc. 2003, 125, 3268-3272.
20. (e) Kirby, A. J.; Komarov, I. V.; Wothers, P. D.; Feeder, N. Angew. Chem., Int. Ed. 1998, 37, 785-786.
21. (f) Lease, T. G.; Shea, K. J. J. Am. Chem. Soc. 1993, 115, 2248-2260.
22. (a) Bennet, A.; Somayaji, V.; Brown, R.; Santarsiero, B. D. J. Am. Chem. Soc. 1991, 113, 7563-7571.
23. (b) Somayaji, V.; Brown, R. S. J. Org. Chem. 1986, 51, 2676-2686.
24. (a) Ashimori, A.; Bachand, B.; Calter, M. A.; Govek, S. P.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120, 6488-6499.
25. Dunitz, J., D.; Winkler, F. K. Acta Crystallogr. 1975, B31, 251-263.
26. 3 atom χ = 60°. See also: Winkler, F. K.; Dunitz, J. D. J. Mol. Biol. 1971, 59, 169-182.
27. (a) Donets, P. A.; Van der Eycken, E. V. Org. Lett. 2007, 9, 3017-3020.
28. (b) Larock, R., C.; Johnson, P., L. J. Chem. Soc., Chem. Commun. 1989, 1368-1370.
29. For a review, see: Fagnou, K.; Lautens, M. Chem. Rev. 2003, 103, 169-196.