Preparation of 2-diazo-2-oxopiperidin-3-yl-3-oxopropanoates. Useful reagents for Rh(II)-catalyzed cyclization-cycloaddition chemistry

Arkivoc

Volumn 2007, Issue 5, 2007, Pages 125-138

  Hong, Xuechuan ^a   Mejía Oneto, José M ^a   France, Stefan ^a   Padwa, Albert ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

Coupling; Diazo imide; Indole; Lactam; Rhodium(II); Synthesis

Indexed keywords

EID: 33846151088     PISSN: 1551-7012     EISSN: 14246376     Source Type: Journal    
DOI: 10.3998/ark.5550190.0008.511     Document Type: Article

References (62)

1. Braekman, J. C.; Daloze, D. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1990; Vol. 6, pp 421-466.
2. Elbein, A.; Molyneux, R. I. In The Alkaloids, Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley: New York, 1990; Vol. 5, pp 1-54.
3. Saxton, J. E. In The Alkaloids, Chemistry and Biology; Cordell, G. A., Ed.; Academic Press: San Diego, CA, 1998: Vol. 5, pp 1-197.
4. Saxton, J. E. Indoles, Part 4: The Monoterpenoid Indole Alkaloids; Wiley: Chichester, 1983.
5. Herbert, R. B. In The Monoterpenoid Indole Alkaloids; Supplement to Vol. 25, Part 4 of The Chemistry of Heterocyclic Compounds; Saxton, J. E., Ed.; Wiley: Chichester, 1994; Chapter 1.
6. Toyota, M.; Ihara, M. Nat. Prod. Rep. 1998, 327 and references therein.
7. For the first synthesis of aspidospermine and vindoline, see: Stork, G.; Dolfini, J. E. J. Am. Chem. Soc. 1963, 85, 2872.
8. Ando, M.; Buchi, G.; Ohnuma, T. J. Am. Chem. Soc. 1975, 97, 6880.
9. For some select methods to synthesize the pentacyclic framework of aspidospermidine (1), see: Camerman, A.; Camerman, N.; Kutney, J. P.; Piers, E.; Trotter, J. Tetrahedron Lett. 1965, 637.
10. Harley-Mason, J.; Kaplan, M. J. Chem. Soc., Chem. Commun. 1967, 915.
11. Laronze, J. -Y.; Laronze-Fontaine, J.; Lévy, J.; Le Men, J. Tetrahedron Lett. 1974, 491.
12. Ban, Y.; Yoshida, K.; Goto, J.; Oishi, T. J. Am. Chem. Soc. 1981, 103, 6990.
13. Gallagher, T.; Magnus, P.; Huffman, J. J. Am. Chem. Soc. 1982, 104, 1140.
14. Wenkert, E.; Hudlicky, T. J. Org. Chem. 1988, 53, 1953.
15. Mandal, S. B.; Giri, V. S.; Sabeena, M. S.; Pakrashi, S. C. J. Org. Chem. 1988, 53, 4236.
16. Meyers, A. I.; Berney, D. J. Org. Chem. 1989, 54, 4673.
17. Node, M.; Nagasawa, H.; Fugi, K. J. Org. Chem. 1990, 55, 517.
18. Le Menez, P.; Kunesch, N.; Lui, S.; Wenkert, E. J. Org. Chem. 1991, 56, 2915.
19. Desmaële, D.; d'Angelo, J. J. Org. Chem. 1994, 59, 2292.
20. Wenkert, E.; Lui, S. J. Org. Chem. 1994, 59, 7677.
21. Forns, P.; Diez, A.; Rubiralta, M. J. Org. Chem. 1996, 61, 7882.
22. Schultz, A. G.; Pettus, L. J. Org. Chem. 1997, 62, 6855.
23. Callaghan, O.; Lampard, C.; Kennedy, A. R.; Murphy, J. A. J. Chem. Soc., Perkin Trans. 1 1999, 995.
24. Iyengar, R.; Schildknegt, K.; Aubé, J. Org. Lett. 2000, 2, 1625.
25. Toczko, M. A.; Heathcock, C. H. J. Org. Chem. 2000, 65, 2642.
26. Patro, B.; Murphy, J. A. Org. Lett. 2000, 2, 3599.
27. Kozmin, S. A.; Iwama, T.; Huang, Y.; Rawal, V. H. J. Am. Chem. Soc. 2002, 124, 4628.
28. Banwell, M. G.; Smith, J. A. J. Chem. Soc., Perkin Trans. 1 2002, 2613.
29. Marino, J. P.; Rubio, M. B.; Cao, G.; de Dios, A. J. Am. Chem. Soc. 2002, 124, 13398.
30. Gnecco, D.; Vázquez, E.; Galindo, A.; Terán, J. L.; Bernès, S.; Enríquez, R. G. Arkivoc 2003, 11, 185.
31. Tanino, H.; Fukuishi, T.; Ushiyama, M.; Okada, K. Tetrahedron 2004, 60, 3273.
32. Banwell, M. G.; Lupton, D. W. Org. Biomol. Chem. 2005, 3, 213.
33. For some leading references, see: Padwa, A.; Hornbuckle, S. F. Chem. Rev. 1991, 91, 263.
34. Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223.
35. Padwa, A. Top. Curr. Chem. 1997, 189, 121.
36. Padwa, A. Pure Appl. Chem. 2004, 76, 1933.
37. Padwa, A.; Brodney, M. A.; Lynch, S. M.; Rashatasakhon, P.; Wang, Q.; Zhang, H. J. Org. Chem. 2004, 69, 3735.
38. Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; John Wiley & Sons; New York, 1998.
39. Padwa, A.; Carter, S. P.; Nimmesgern, H. J. Org. Chem. 1986, 51, 1157.
40. Padwa, A.; Carter, S. P.; Nimmesgern, H.; Stull, P. D. J. Am. Chem. Soc. 1988, 110, 2894.
41. Padwa, A.; Stull, P. D. Tetrahedron Lett. 1987, 28, 5407.
42. Padwa, A.; Fryxell, G. E.; Zhi, L. J. Org. Chem. 1988, 53, 2877.
43. Padwa, A.; Fryxell, G. E.; Zhi, L. J. Am. Chem. Soc. 1990, 112, 3100.
44. Curtis, E. A.; Worsencroft, K. J.; Padwa, A. Tetrahedron Lett. 1997, 38, 3319.
45. Dean, D. C.; Krumpe, K. E.; Padwa, A. J. Chem. Soc., Chem. Commun. 1989, 921.
46. Doyle, M. P. Chem. Rev. 1986, 86, 919.
47. Adams, J.; Spero, D. M. Tetrahedron 1991, 47, 1765.
48. Padwa, A.; Marino, J. P., Jr.; Osterhout, M. H. J. Org. Chem. 1995, 60, 2704.
49. Padwa, A.; Marino, J. P., Jr.; Osterhout, M. H.; Price, A. T.; Semones, M. A. J. Org. Chem. 1994, 59, 5518.
50. Hertzog, D. L.; Nadler, W. R.; Osterhout, M. H.; Price, A. T. J. Org. Chem. 1994, 59, 1418.
51. Hertzog, D. L.; Austin, D. J.; Nadler, W. R.; Padwa, A. Tetrahedron Lett. 1992, 33, 4731.
52. Osterhout, M. H.; Nadler, W. R.; Padwa, A. Synthesis 1994, 123.
53. Weingarten, M. D.; Prein, M.; Price, A. T.; Snyder, J. P.; Padwa, A. J. Org. Chem. 1997, 62, 2001.
54. Padwa, A.; Price, A. T. J. Org. Chem. 1995, 60, 6258.
55. Padwa, A.; Price, A. T. J. Org. Chem. 1998, 63, 556.
56. Mejía-Oneto, J. M.; Padwa, A. Org. Lett. 2004, 6, 3241.
57. Padwa, A.; Lynch, S. M.; Mejía-Oneto, J. M.; Zhang, H. J. Org. Chem. 2005, 70, 2206.
58. Mejía-Oneto, J. M.; Padwa, A. Org. Lett. 2006, 8, 3275.
59. Marino, J. P., Jr.; Osterhout, M. H.; Price, A. T.; Sheehan, S. M.; Padwa, A. Tetrahedron Lett. 1994, 35, 849.
60. Regitz, M. Chem. Ber. 1966, 99, 3128.
61. Regitz, M.; Hocker, J.; Liedhegener, A. Org. Synth. 1973, 5, 179.
62. Brooks, D. W.; Lu, D. L.; Masamune, S. Angew. Chem., Int. Ed. 1979, 18, 72.