A one-pot formal [4 + 2] cycloaddition approach to substituted piperidines, indolizidines, and quinolizidines. Total synthesis of indolizidine (-)-209I

Journal of Organic Chemistry

Volumn 70, Issue 18, 2005, Pages 7364-7370

  Yu, Shanghai ^a   Zhu, Wei ^a   Ma, Dawei ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; HEATING; SODIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

INDOLIZIDINES; MICHAEL ADDITION/ALKYLATION PROCESSES; PIPERIDINES; QUINOLIZIDINES;

ORGANIC COMPOUNDS;

ALKYNE; HEXANOIC ACID; INDOLIZIDINE DERIVATIVE; METHYL 2 HEXENOATE; PIPERIDINE DERIVATIVE; PROPYLAMINE; QUINOLIZIDINE DERIVATIVE; SODIUM CARBONATE; SODIUM IODIDE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CYCLOADDITION; DRUG SYNTHESIS; HEATING; MICHAEL ADDITION; STEREOCHEMISTRY;

INDOLIZINES;

EID: 24144471792     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051080y     Document Type: Article

References (45)

1. For recent reviews, see: (a) Weintraub, P. M.; Sabol, J. S.; Kane, J. M.; Borcherding, D. R. Tetrahedron 2003, 59, 2953.
2. (b) Daly, J. W. J. Med. Chem. 2003, 46, 445.
3. (c) Michael, J. P. Nat. Prod. Rep. 2004, 21, 625.
4. (d) Buffat, M. G. P. Tetrahedron 2004, 60, 1701.
5. (e) Harrity, J. P. A.; Provoost, O. Org. Biomol. Chem. 2005, 3, 1349.
6. For recent examples, see: (a) Chen, Z. M.; Davies, E.; Miller, W. S.; Shan, S.; Valenzano, K. J.; Kyle, D. J. Bioorg. Med. Chem. Lett. 2004, 14, 5275.
7. (b) Jong, L.; Zaveri, N.; Toll, L. Bioorg. Med. Chem. Lett. 2004, 14, 181.
8. (c) Sparatore, A.; Novelli, F. Med. Chem. Res. 2002, 11, 1.
9. (d) Matsuda, H.; Shimoda, H.; Yoshikawa, M. Bioorg. Med. Chem. 2001, 9, 1031.
10. (e) Combrink, K. D.; Gulgeze, H. B.; Yu, K.-L.; Pearce, B. C.; Trehan, A. K.; Wei, J.; Deshpande, M.; Krystal, M.; Torri, A.; Luo, G.; Cianci, C.; Danetz, S.; Tiley, L.; Meanwell, N. A. Bioorg. Med. Chem. Lett. 2000, 10, 164.
11. For recent leading references, see: (a) Cassidy, M. P.; Padwa, A. Org. Lett, 2004, 6, 4029.
12. (b) Poupon, E.; Francois, D.; Kunesch, N.; Husson, H. P. J. Org. Chem. 2004, 69, 3836.
13. (c) Zech, G.; Kunz, H. Chem.-Eur. J. 2004, 10, 4136.
14. (d) Kuethe, J. T.; Comins, D. L. J. Org. Chem. 2004, 69, 5219.
15. (e) Wrobleski, A.; Sahasrabudhe, K.; Aubé, J. J. Am. Chem. Soc. 2004, 126, 5475.
16. (f) Singh, O. V.; Han, H. Org. Lett. 2004, 6, 3067.
17. (g) Smith, A. B. Kim, D. S. Org. Lett. 2004, 6, 1493.
18. (h) Amos, D. T.; Renslo, A. R.; Danheiser, R. L. J. Am. Chem. Soc. 2003, 125, 4970.
19. (i) Molander, G. A.; Pack, S. K. J. Org. Chem. 2003, 68, 9214.
20. (j) Randl, S.; Blechert, S. J. Org. Chem. 2003, 68, 8879.
21. (k) Gracias, V.; Zeng, Y.; Desai, P.; Aubé, J. Org. Lett. 2003, 5, 4999.
22. (l) Huang, H.; Spande, T. F.; Panek, J. S. J. Am. Chem. Soc. 2003, 125, 626.
23. (m) Alcaide, B.; Almendros, P.; Alonso, J. M.; Aly, M. F. Chem.-Eur. J. 2003, 9, 3415.
24. (n) Davis, F. A.; Yang, B. Org. Lett. 2003, 5, 5011.
25. (o) Toyooka, N.; Nemoto, H. Tetrahedron Lett. 2003, 44, 569.
26. (s) Sato, T.; Aoyagi, S.; Kibayashi, C. Org. Lett. 2003, 5, 3839.
27. (a) Barluenga, J.; Mateos, C.; Aznar, F.; Valdés, C. Org. Lett. 2002, 4, 1971.
28. (b) Collin, J.; Jaber, N.; Lannou, M. I. Tetrahedron Lett. 2001, 42, 7405.
29. (c) Domingo, L. R. Tetrahedron 2002, 58, 3765.
30. (d) Kobayashi, S.; Kusakabe, K.; Ishitani, H. Org. Lett. 2000, 2, 1225.
31. Takasu, K.; Nishida, N.; Ihara, M. Tetrahedron Lett. 2003, 44, 7429.
32. (a) Back, T. G.; Nakajima, K. Org. Lett. 1999, 1, 261.
33. (b) Back, T. G.; Nakajima, K. J. Org. Chem. 2000, 65, 4543.
34. (a) Zhu, W.; Dong, D.; Pu, X.; Ma, D. Org. Lett. 2005, 7, 705.
35. For related studies from this group, see: (b) Pu, X.; Ma, D. J. Org. Chem. 2003, 68, 4400.
36. (c) Ma, D.; Zhu, W. Org. Lett. 2001, 3, 3927.
37. (d) Ma, D.; Sun, H. J. Org. Chem. 2000, 65, 6009.
38. (e) Ma, D.; Sun, H. Org. Lett. 2000, 2, 2503.
39. (f) Ma, D.; Zhang, J. Tetrahedron Lett. 1998, 39, 9067.
40. Cassai, J. M.; Furst, A.; Meier, W. Helv. Chim. Acta 1976, 59, 1917.
41. Parkes, K. E. B.; Bushnell, D. J.; Crazkett, P. H.; Dundson, S. J.; Freeman, A. C.; Gunn, M. P.; Hopkins, R. A.; Lambert, R. W.; Martin, J. A.; Merrett, J. H.; Redshaw, S.; Spurden, W. C.; Thomas, G. J. J. Org. Chem. 1994, 59, 3656.
42. Isolation: (a) Toyooka, N.; Tanaka, K.; Momose, T.; Daly, J. W.; Garraffo, H. M. Tetrahedron 1997, 53, 9553.
43. For synthesis, see: (b) Michel, P.; Rassat, A.; Daly, J. W.; Spande, T. F. J. Org. Chem. 2000, 65, 8908.
44. (c) Enders, D.; Thiebes, C. Synlett 2000, 1745.
45. Davies, S. G.; Ichihara, O.; Walters, I. S. J. Chem. Soc., Perkin Trans, 1 1994, 1141.