Pure Appl. Chem., 2009, Vol. 81, No. 2, pp. 217-226
http://dx.doi.org/10.1351/PAC-CON-08-07-14
Indium-catalyzed Conia-ene reaction for alkaloid synthesis
References
- 1. H. Ooi, N. Ishibashi, Y. Iwabuchi, J. Ishihara, S. Hatakeyama. J. Org. Chem. 69, 7765 (2004). (http://dx.doi.org/10.1021/jo048817o)
- 2. E. O. Onyango, J. Tsurumoto, N. Imai, K. Takahashi, J. Ishihara, S. Hatakeyama. Angew. Chem., Int. Ed. 46, 6703 (2007). (http://dx.doi.org/10.1002/anie.200702229)
- 3. K. Takahashi, M. Midori, K. Kawano, J. Ishihara, S. Hatakeyama. Angew. Chem., Int. Ed. 47, 6244 (2008). (http://dx.doi.org/10.1002/anie.200704423)
- 4. K. Takahashi, M. Midori, J. Ishihara, S. Hatakeyama. In 49th 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). (http://dx.doi.org/10.1002/asia.200600310)
- 6. Review: J. M. Conia, P. L. Percheg. Synthesis 1 (1975). (http://dx.doi.org/10.1055/s-1975-23652)
- 7. (a). J. J. Kennedy-Smith, S. T. Staben, F. D. Toste. J. Am. Chem. Soc. 126, 4526 (2004); (http://dx.doi.org/10.1021/ja049487s)
- 7. (b). S. T. Staben, J. J. Kennedy-Smith, F. D. Toste. Angew. Chem., Int. Ed. 43, 5350 (2004); (http://dx.doi.org/10.1002/anie.200460844)
- 7. (c). Q. Gao, B.F. Zheng, J. H. Li, D. Yang. Org. Lett. 7, 2185 (2005); (http://dx.doi.org/10.1021/ol050532q)
- 7. (d). A. Ochida, H. Ito, M. Sawamura. J. Am. Chem. Soc. 128, 16486 (2006); (http://dx.doi.org/10.1021/ja066800c)
- 7. (e). B. K. Corkey, F. D. Toste. J. Am. Chem. Soc. 129, 2764 (2007); (http://dx.doi.org/10.1021/ja068723r)
- 7. (f). H. Tsuji, K. Yamagata, Y. Itoh, K. Endo, M. Nakamura, E. Nakamura. Angew. Chem., Int. Ed. 46, 8060 (2007); (http://dx.doi.org/10.1002/anie.200702928)
- 7. (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.
- 8. 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.
- 9. (a). X. Marat, N. Monteiro, G. Balme. Synlett 845 (1997); (http://dx.doi.org/10.1055/s-1997-5755)
- 9. (b). B. Clique, N. Monteiro, G. Balme. Tetrahedron Lett. 40, 1301 (1999); (http://dx.doi.org/10.1016/S0040-4039(98)02631-8)
- 9. (c). M. Cavicchioli, X. Marat, N. Monteiro, B. Hartmann, G. Balme. Tetrahedron Lett. 43, 2609 (2002); (http://dx.doi.org/10.1016/S0040-4039(02)00313-1)
- 9. (d). M. Nakamura, C. Liang, E. Nakamura. Org. Lett. 6, 2015 (2004); (http://dx.doi.org/10.1021/ol0493554)
- 9. (e). S. Morikawa, S. Yamazaki, Y. Furusaki, N. Amano, K. Zenke, K. Kakiuchi. J. Org. Chem. 71, 3540 (2006). (http://dx.doi.org/10.1021/jo0602118)
- 10. (a). E. C. Minnihan, S. L. Colletti, F. D. Toste, H. C. Shen. J. Org. Chem. 72, 6287 (2007); (http://dx.doi.org/10.1021/jo071014r)
- 10. (b). C.-Y. Zhou, C.-M. Che. J. Am. Chem. Soc. 129, 5828 (2007). (http://dx.doi.org/10.1021/ja070027j)
- 11. R. H. Feling, G. O. Buchanan, T. J. Mincer, C. A. Kauffman, P. R. Jensen, W. Fenical. Angew. Chem., Int. Ed. 43, 355 (2003). (http://dx.doi.org/10.1002/anie.200390115)
- 12. (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); (http://dx.doi.org/10.1016/j.ccr.2005.10.013)
- 12. (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). (http://dx.doi.org/10.1021/jm048995+)
- 13. M. Groll, R. Huber, B. C. M. Potts. J. Am. Chem. Soc. 128, 5136 (2006). (http://dx.doi.org/10.1021/ja058320b)
- 14. (a). E. J. Corey, P. Saravanan, L. R. Reddy. J. Am. Chem. Soc. 126, 6230 (2004); (http://dx.doi.org/10.1021/ja048613p)
- 14. (b). L. R. Reddy, J.-F. Fournier, B. V. S. Reddy, E. J. Corey. Org. Lett. 7, 2699 (2005); (http://dx.doi.org/10.1021/ol0508734)
- 14. (c). S. J. Danishefsky, A. Endo. J. Am. Chem. Soc. 127, 8298 (2005); (http://dx.doi.org/10.1021/ja0522783)
- 14. (d). T. Ling, V. R. Macherla, R. R. Manam, K. A. McArthur, B. C. M. Potts. Org. Lett. 9, 2289 (2007); (http://dx.doi.org/10.1021/ol0706051)
- 14. (e). T. Fukuda, K. Sugiyama, S. Arima, Y. Harigaya, T. Nagamitsu, S. Omura. Org. Lett. 10, 4239 (2008); (http://dx.doi.org/10.1021/ol8016066)
- 14. (f). N. P. Mulholland, G. Pattenden, I. A. S. Walters. Org. Biomol. Chem. 4, 2845 (2006); (http://dx.doi.org/10.1039/b607109k)
- 14. (g). G. Ma, H. Nguyen, D. Romo. Org. Lett. 9, 2143 (2007); (http://dx.doi.org/10.1021/ol070616u)
- 14. (h). V. Caubert, J. Masse, P. Retailleau, N. Langlois. Tetrahedron Lett. 48, 381 (2007); (http://dx.doi.org/10.1016/j.tetlet.2006.11.087)
- 14. (i). I. V. Margalef, L. Rupnicki, H. W. Lam. Tetrahedron 64, 7896 (2008). (http://dx.doi.org/10.1016/j.tet.2008.06.038)
- 15. J. A. Marshall. J. Org. Chem. 72, 8153 (2007) and refs. therein.
- 16. For example, the exo olefin instantaneously isomerized to the conjugated position under methanolytic conditions using K2CO3.
- 17. B. V. S. Reddy, L. R. Reddy, E. J. Corey. Tetrahedron Lett. 46, 4589 (2005). (http://dx.doi.org/10.1016/j.tetlet.2005.05.003)
- 18. (a). T. Mori, K. Takahashi, M. Kashiwabara, D. Uemura. Tetrahedron Lett. 26, 1073 (1985); (http://dx.doi.org/10.1016/S0040-4039(00)98515-0)
- 18. (b). K. Takahashi, M. Kawabata, D. Uemura. Tetrahedron Lett. 26, 1077 (1985). (http://dx.doi.org/10.1016/S0040-4039(00)98516-2)
- 19. For review: M. G. Moloney, P. C. Trippier, M. Yaqoob, A. Wang. Curr. Drug Discov. Technol. 1, 181 (2004). (http://dx.doi.org/10.2174/1570163043334974)
- 20. (a). T. J. Donohoe, J. Y. K. Chiu, R. E. Thomas. Org. Lett. 9, 421 (2007); (http://dx.doi.org/10.1021/ol062705x)
- 20. (b). N. J. Bennet, J. C. Prodger, G. Pattenden. Tetrahedron 63, 6216 (2007) and refs. therein.
- 21. A. S. Kende, K. Kawamura, R. J. DeVita. J. Am. Chem. Soc. 112, 4070 (1990). (http://dx.doi.org/10.1021/ja00166a072)
- 22. The NOESY spectrum was taken in [D8]THF/D2O (3:1) which was the same solvent system as that employed for the osmylation.
- 23. Conformer 44 was suggested to be the energetically most stable by molecular mechanics calculations (MMFF, Macro Model 8.5).
- 24. T. Fujisawa, T. Mori, T. Sato. Chem. Lett. 835 (1983). (http://dx.doi.org/10.1246/cl.1983.835)
- 25. J. S. Panek, P. Liu. J. Am. Chem. Soc. 122, 11090 (2000). (http://dx.doi.org/10.1021/ja002377a)
- 26. N. Henaff, A. Whiting. Org. Lett. 1, 1137 (1999). (http://dx.doi.org/10.1021/ol990967b)
- 27. Y. Watanabe. WO 2003006422.
- 28. (a). C. M. Shafer, T. F. Molinsky. J. Org. Chem. 63, 551 (1998); (http://dx.doi.org/10.1021/jo971410h)
- 28. (b). J. P. Marino, H. N. Nguyen. Tetrahedron Lett. 44, 7395 (2003). (http://dx.doi.org/10.1016/j.tetlet.2003.08.044)