Spiro-fused pyrrolidine, piperidine, and oxindole scaffolds from lactams

Organic Letters

Volumn 14, Issue 18, 2012, Pages 4846-4849

  Hirschhäuser, Christoph ^a   Parker, Jeremy S ^b   Perry, Matthew W D ^c   Haddow, Mairi F ^a   Gallagher, Timothy ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

^c ASTRAZENECA R AND D   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE DERIVATIVE; COERULESCINE; HORSFILINE; INDOLE DERIVATIVE; LACTAM; OXINDOLE; PIPERIDINE; PIPERIDINE DERIVATIVE; PYRROLIDINE; PYRROLIDINE DERIVATIVE; SPIRO COMPOUND;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ANILINE COMPOUNDS; CATALYSIS; INDOLES; LACTAMS; MOLECULAR STRUCTURE; PIPERIDINES; PYRROLIDINES; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 84868225054     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol302176z     Document Type: Article

References (24)

1. Congreve, M.; Carr, R.; Murray, C.; Jhoti, H. Drug Discov. Today 2003, 8, 876-877.
2. (a) Bower, J. F.; Švenda, J.; Williams, A. J.; Charmant, J. P. H.; Lawrence, R. M.; Szeto, P.; Gallagher, T. Org. Lett. 2004, 6, 4727-4730. For reviews, see
3. (b) Meléndez, R. E.; Lubell, W. D. Tetrahedron 2003, 59, 2581-2616
4. (c) Bower, J. F.; Rujirawanich, J.; Gallagher, T. Org. Biomol. Chem. 2010, 8, 1505-1519.
5. (a) Yamashita, T.; Kamata, M.; Endo, S.; Yamamoto, M.; Kakegawa, K.; Watanabe, H.; Miwa, K.; Yamano, T.; Funata, M.; Sakamoto, J.; Tani, A.; Mol, C. D.; Zou, H.; Dougan, D. R.; Sang, B.; Snell, G.; Fukatsu, K. Bioorg. Med. Chem. Lett. 2011, 21, 6314-6318
6. (b) Converso, A.; Hartingh, T.; Garbaccio, R. M.; Tasber, E.; Rickert, K.; Fraley, M. E.; Yan, Y.; Kreatsoulas, C.; Stirdivant, S.; Drakas, B.; Walsh, E. S.; Hamilton, K.; Buser, C. A.; Mao, X.; Abrams,M. T.; Beck, S. C.; Tao, W.; Lobell, R.; Sepp-Lorenzino, L.; Zugay-Murphy, J.; Sardana, V.; Munshi, S. K.; Jezequel-Sur, S. M.; Zuck, P. D.; Hartman, G. D. Bioorg. Med. Chem. Lett. 2009, 19, 1240-1244
7. (c) Kaptein, A.; Oubrie, A.; de Zwart, E.; Hoogenboom, N.; de Wit, J.; van de Kar, B.; van Hoek, M.; Vogel, G.; de Kimpe, V.; Schultz-Fademrecht, C.; Borsboom, J.; van Zeeland, M.; Versteegh, J.; Kazemier, B.; de Roos, J.; Wijnands, F.; Dulos, J.; Jaeger, M.; Leandro-Garcia, P.; Barf, T. Bioorg. Med. Chem. Lett. 2011, 21, 3823-3827
8. (d) Sippy, K. B.; Anderson, D. J.; Bunnelle, W. H.; Hutchins, C. W.; Schrimpf, M. R. Bioorg.Med. Chem.Lett. 2009, 19, 1682-1685
9. (e) Hansen, J. D.;Newhouse, B. J.; Allen, S.; Anderson, A.; Eary, T.; Schiro, J.;Gaudino, J.; Laird, E.; Allen, A. C.; Chantry, D.; Eberhardt, C.; Burgess, L. E. Tetrahedron Lett. 2006, 47, 69-72.
10. For example: (Manzamines) (a) Magnier, E.; Langlois, Y. Tetrahedron 1998, 54, 6201-6258 (Horsfiline)
11. (b) Jossang, A.; Jossang, P.; Hadi, H. A.; Sevenet, T.; Bodo, B. J. Org. Chem. 1991, 56, 6527-6530.
12. (a) Stanetty, P.; Turner, M.; Mihovilovic, M. Molecules 2005, 10, 367- 375
13. (b) Gallagher, T.; Derrick, I.; Durkin, P. M.; Haseler, C. A.; Hirschhäuser, C.; Magrone, P. J. Org. Chem. 2010, 75, 3766-3774. For preparation of 7, see
14. (c) Hirschhäuser, C.; Haseler, C. A.; Gallagher, T. Angew. Chem., Int. Ed. 2011, 50, 5162-5165. For access to enantimerically pure precursors, see
15. (d) Lima, E. C.; Domingos, J. L. O.; Dias, A. G.; Costa, P. R. R. Tetrahedron: Asymmetry 2008, 19, 1161-1165
16. (e) Galeazzi, R.; Martelli, G.Mobbili, G.; Orena, M.; Panagiotaki, M. Heterocycles 2003, 60, 2485-2498
17. (f) Gray, D.;Gallagher, T. Angew. Chem., Int. Ed. 2006, 45, 2419-2423.
18. For a reagent-controlled aproach, see: Moss, T. A.; Alonso, B.; Fenwick, D. R.; Dixon, D. J. Angew. Chem., Int. Ed. 2009, 49, 568-571.
19. Kyasa, S.; Fisher, T.; Dussault, P. Synthesis 2011, 3475-3481.
20. (a) Bella, M.; Kobbelgaard, S.; Jørgensen, K. A. J. Am. Chem. Soc. 2005, 127, 3670-3671
21. (b) Cowley, A. R.; Hill, T. J.; Kocis, P.; Moloney, M. G.; Stevenson, R. D.; Thompson, A. L. Org. Biomol. Chem. 2011, 9, 7042
22. (c) Sen, S.; Potti, V. R.; Surakanti, R.; Murthy, Y.L.N.; Pallepogu, R. Org. Biomol. Chem. 2011, 9, 358
23. (d) Kobbelgaard, S.; Bella,M.; Jørgensen, K. A. J. Org. Chem. 2006, 71, 4980-4987.
24. Kulkarni, M. G.; Dhondge, A. P.; Chavhan, S. W.; Borhade, A. S.; Shaikh, Y. B.; Birhade, D. R.; Desai, M. P.; Dhatrak, N. R. Beilstein J. Org. Chem. 2010, 6, 876-879.