Indium-catalyzed Conia-ene reaction for alkaloid synthesis

Pure and Applied Chemistry

Volumn 81, Issue 2, 2009, Pages 217-226

  Hatakeyama, Susumi ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

Alkaloids; Conia ene reaction; Neooxazolomycin; Salinosporamide A; Total synthesis

Indexed keywords

EID: 61449241709     PISSN: 00334545     EISSN: 13653075     Source Type: Journal    
DOI: 10.1351/PAC-CON-08-07-14     Document Type: Conference Paper

References (51)

1. H. Ooi, N. Ishibashi, Y. Iwabuchi, J. Ishihara, S. Hatakeyama. J. Org. Chem. 69, 7765 (2004).
2. E. O. Onyango, J. Tsurumoto, N. Imai, K. Takahashi, J. Ishihara, S. Hatakeyama. Angew. Chem., Int. Ed. 46, 6703 (2007).
3. K. Takahashi, M. Midori, K. Kawano, J. Ishihara, S. Hatakeyama. Angew. Chem., Int. Ed. 47, 6244 (2008).
4. th Symposium on the Chemistry of Natural Products, symposium papers, pp. 133-138 (2007).
5. Review: M. Shibasaki, M. Kanai, N. Fukuda. Chem. Asian J. 2, 20 (2007).
6. Review: J. M. Conia, P. L. Percheg. Synthesis 1 (1975).
7. (a) J. J. Kennedy-Smith, S. T. Staben, F. D. Toste. J. Am. Chem. Soc. 126, 4526 (2004);
8. (b) S. T. Staben, J. J. Kennedy-Smith, F. D. Toste. Angew. Chem., Int. Ed. 43, 5350 (2004);
9. (c) Q. Gao, B.-F. Zheng, J. H. Li, D. Yang. Org. Lett. 7, 2185 (2005);
10. (d) A. Ochida, H. Ito, M. Sawamura. J. Am. Chem. Soc. 128, 16486 (2006);
11. (e) B. K. Corkey, F. D. Toste. J. Am. Chem. Soc. 129, 2764 (2007);
12. (f) H. Tsuji, K. Yamagata, Y. Itoh, K. Endo, M. Nakamura, E. Nakamura. Angew. Chem., Int. Ed. 46, 8060 (2007);
13. (g) Y. Itoh, H. Tsuji, K. Yamagata, K. Endo, I. Tanaka, M. Nakamura, E. Nakamura. J. Am. Chem. Soc. 130, 17161 (2008) and refs. therein.
14. For an intermolecular version of the Conia-ene reaction: K. Endo, T. Hatakeyama, M. Nakamura, E. Nakamura. J. Am. Chem. Soc. 129, 5264 (2007) and refs. therein.
15. For related metal-catalyzed cyclizations producing 3-methylene- pyrrolidines and tetrahydrofurans: (a) X. Marat, N. Monteiro, G. Balme. Synlett 845 (1997);
16. (b) B. Clique, N. Monteiro, G. Balme. Tetrahedron Lett. 40, 1301 (1999);
17. (c) M. Cavicchioli, X. Marat, N. Monteiro, B. Hartmann, G. Balme. Tetrahedron Lett. 43, 2609 (2002);
18. (d) M. Nakamura, C. Liang, E. Nakamura. Org. Lett. 6, 2015 (2004);
19. (e) S. Morikawa, S. Yamazaki, Y. Furusaki, N. Amano, K. Zenke, K. Kakiuchi. J. Org. Chem. 71, 3540 (2006).
20. For related metal-catalyzed cyclizations producing lactams: (a) E. C. Minnihan, S. L. Colletti, F. D. Toste, H. C. Shen. J. Org. Chem. 72, 6287 (2007);
21. (b) C.-Y. Zhou, C.-M. Che. J. Am. Chem. Soc. 129, 5828 (2007).
22. R. H. Feling, G. O. Buchanan, T. J. Mincer, C. A. Kauffman, P. R. Jensen, W. Fenical. Angew. Chem., Int. Ed. 43, 355 (2003).
23. (a) D. Chauhan, L. Catley, G. Li, K. Podar, T. Hideshima, M. Velankar, C. Mitsiades, N. Mitsiades, H. Yasui, A. Letai, H. Ovaa, C. Berkers, B. Nicholson, T.-H. Chao, S. T. C. Neuteboom, P. Richardson, M. A. Palladino, K. C. Anderson. Cancer Cell 8, 407 (2005);
24. (b) V. R. Macherla, S. S. Mitchell, P. R. Manam, K. A. Reed, T.-H. Chao, B. Nicholson, G. Deyanat-Yazdi, B. Mai, P. R. Jensen, W. Fenical, S. T. C. Neuteboom, K. S. Lam, M. A. Palladino, B. C. M. Potts. J. Med. Chem. 48, 3684 (2005).
25. M. Groll, R. Huber, B. C. M. Potts. J. Am. Chem. Soc. 128, 5136 (2006).
26. Total synthesis: (a) E. J. Corey, P. Saravanan, L. R. Reddy. J. Am. Chem. Soc. 126, 6230 (2004);
27. (b) L. R. Reddy, J.-F. Fournier, B. V. S. Reddy, E. J. Corey. Org. Lett. 7, 2699 (2005);
28. (c) S. J. Danishefsky, A. Endo. J. Am. Chem. Soc. 127, 8298 (2005);
29. (d) T. Ling, V. R. Macherla, R. R. Manam, K. A. McArthur, B. C. M. Potts. Org. Lett. 9, 2289 (2007);
30. (e) T. Fukuda, K. Sugiyama, S. Arima, Y. Harigaya, T. Nagamitsu, S. Omura. Org. Lett. 10, 4239 (2008);
31. racemic synthesis: (f) N. P. Mulholland, G. Pattenden, I. A. S. Walters. Org. Biomol. Chem. 4, 2845 (2006);
32. (g) G. Ma, H. Nguyen, D. Romo. Org. Lett. 9, 2143 (2007);
33. formal synthesis: (h) V. Caubert, J. Masse, P. Retailleau, N. Langlois. Tetrahedron Lett. 48, 381 (2007);
34. (i) I. V. Margalef, L. Rupnicki, H. W. Lam. Tetrahedron 64, 7896 (2008).
35. J. A. Marshall. J. Org. Chem. 72, 8153 (2007) and refs. therein.
36. For example, the exo olefin instantaneously isomerized to the conjugated position under methanolytic conditions using K2CO3.
37. B. V. S. Reddy, L. R. Reddy, E. J. Corey. Tetrahedron Lett. 46, 4589 (2005).
38. (a) T. Mori, K. Takahashi, M. Kashiwabara, D. Uemura. Tetrahedron Lett. 26, 1073 (1985);
39. (b) K. Takahashi, M. Kawabata, D. Uemura. Tetrahedron Lett. 26, 1077 (1985).
40. For review: M. G. Moloney, P. C. Trippier, M. Yaqoob, A. Wang. Curr. Drug Discov. Technol. 1, 181 (2004).
41. (a) T. J. Donohoe, J. Y. K. Chiu, R. E. Thomas. Org. Lett. 9, 421 (2007);
42. (b) N. J. Bennet, J. C. Prodger, G. Pattenden. Tetrahedron 63, 6216 (2007) and refs. therein.
43. A. S. Kende, K. Kawamura, R. J. DeVita. J. Am. Chem. Soc. 112, 4070 (1990).
44. The NOESY spectrum was taken in [D8]THF/D2O (3:1) which was the same solvent system as that employed for the osmylation.
45. Conformer 44 was suggested to be the energetically most stable by molecular mechanics calculations (MMFF, Macro Model 8.5).
46. T. Fujisawa, T. Mori, T. Sato. Chem. Lett. 835 (1983).
47. J. S. Panek, P. Liu. J. Am. Chem. Soc. 122, 11090 (2000).
48. N. Hénaff, A. Whiting. Org. Lett. 1, 1137 (1999).
49. Y. Watanabe. WO 2003006422.
50. (a) C. M. Shafer, T. F. Molinsky. J. Org. Chem. 63, 551 (1998);
51. (b) J. P. Marino, H. N. Nguyen. Tetrahedron Lett. 44, 7395 (2003).