Abstract
In(OTf)3-catalyzed cyclization of nitrogen- and oxygen-tethered acetylenic malonic esters provides various five- to seven-membered heterocycles in moderate to excellent yield, and the reaction proceeds with no racemization and complete E-selectivity in the case of chiral and nonterminal alkynes. The synthetic utility is demonstrated by the synthesis of (-)-salinosporamide A, a highly potent 20S proteasome inhibitor, and (+)-neooxazolomycin, a member of the oxazolomycin family of antibiotics.
Conference
International Conference on Organic Synthesis (ICOS 17), International Conference on Organic Synthesis, ICOS, Organic Synthesis, 17th, Daejeon, Korea, 2008-06-22–2008-06-27
References
1. doi:10.1021/jo048817o, H. Ooi, N. Ishibashi, Y. Iwabuchi, J. Ishihara, S. Hatakeyama. J. Org. Chem. 69, 7765 (2004).Search in Google Scholar
2. doi:10.1002/anie.200702229, E. O. Onyango, J. Tsurumoto, N. Imai, K. Takahashi, J. Ishihara, S. Hatakeyama. Angew. Chem., Int. Ed. 46, 6703 (2007).Search in Google Scholar
3. doi:10.1002/anie.200704423, K. Takahashi, M. Midori, K. Kawano, J. Ishihara, S. Hatakeyama. Angew. Chem., Int. Ed. 47, 6244 (2008).Search in Google Scholar
4. K. Takahashi, M. Midori, J. Ishihara, S. Hatakeyama. In 49th Symposium on the Chemistry of Natural Products, symposium papers, pp. 133-138 (2007).Search in Google Scholar
5. doi:10.1002/asia.200600310, Review: M. Shibasaki, M. Kanai, N. Fukuda. Chem. Asian J. 2, 20 (2007).Search in Google Scholar
6. doi:10.1055/s-1975-23652, Review: J. M. Conia, P. L. Percheg. Synthesis 1 (1975).Search in Google Scholar
7. (a) doi:10.1021/ja049487s, J. J. Kennedy-Smith, S. T. Staben, F. D. Toste. J. Am. Chem. Soc. 126, 4526 (2004);Search in Google Scholar
7. (b) doi:10.1002/anie.200460844, S. T. Staben, J. J. Kennedy-Smith, F. D. Toste. Angew. Chem., Int. Ed. 43, 5350 (2004);Search in Google Scholar
7. (c) doi:10.1021/ol050532q, Q. Gao, B.F. Zheng, J. H. Li, D. Yang. Org. Lett. 7, 2185 (2005);Search in Google Scholar
7. (d) doi:10.1021/ja066800c, A. Ochida, H. Ito, M. Sawamura. J. Am. Chem. Soc. 128, 16486 (2006);Search in Google Scholar
7. (e) doi:10.1021/ja068723r, B. K. Corkey, F. D. Toste. J. Am. Chem. Soc. 129, 2764 (2007);Search in Google Scholar
7. (f) doi:10.1002/anie.200702928, H. Tsuji, K. Yamagata, Y. Itoh, K. Endo, M. Nakamura, E. Nakamura. Angew. Chem., Int. Ed. 46, 8060 (2007);Search in Google Scholar
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.10.1021/ja805657hSearch in Google Scholar
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.10.1021/ja0702014Search in Google Scholar
9. (a) doi:10.1055/s-1997-5755, X. Marat, N. Monteiro, G. Balme. Synlett 845 (1997);Search in Google Scholar
9. (b) doi:10.1016/S0040-4039(98)02631-8, B. Clique, N. Monteiro, G. Balme. Tetrahedron Lett. 40, 1301 (1999);Search in Google Scholar
9. (c) doi:10.1016/S0040-4039(02)00313-1, M. Cavicchioli, X. Marat, N. Monteiro, B. Hartmann, G. Balme. Tetrahedron Lett. 43, 2609 (2002);Search in Google Scholar
9. (d) doi:10.1021/ol0493554, M. Nakamura, C. Liang, E. Nakamura. Org. Lett. 6, 2015 (2004);Search in Google Scholar
9. (e) doi:10.1021/jo0602118, S. Morikawa, S. Yamazaki, Y. Furusaki, N. Amano, K. Zenke, K. Kakiuchi. J. Org. Chem. 71, 3540 (2006).Search in Google Scholar
10. (a) doi:10.1021/jo071014r, E. C. Minnihan, S. L. Colletti, F. D. Toste, H. C. Shen. J. Org. Chem. 72, 6287 (2007);Search in Google Scholar
10. (b) doi:10.1021/ja070027j, C.-Y. Zhou, C.-M. Che. J. Am. Chem. Soc. 129, 5828 (2007).Search in Google Scholar
11. doi:10.1002/anie.200390115, R. H. Feling, G. O. Buchanan, T. J. Mincer, C. A. Kauffman, P. R. Jensen, W. Fenical. Angew. Chem., Int. Ed. 43, 355 (2003).Search in Google Scholar
12. (a) doi:10.1016/j.ccr.2005.10.013, 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);Search in Google Scholar
12. (b) doi:10.1021/jm048995+, 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).Search in Google Scholar
13. doi:10.1021/ja058320b, M. Groll, R. Huber, B. C. M. Potts. J. Am. Chem. Soc. 128, 5136 (2006).Search in Google Scholar
14. (a) doi:10.1021/ja048613p, E. J. Corey, P. Saravanan, L. R. Reddy. J. Am. Chem. Soc. 126, 6230 (2004);Search in Google Scholar
14. (b) doi:10.1021/ol0508734, L. R. Reddy, J.-F. Fournier, B. V. S. Reddy, E. J. Corey. Org. Lett. 7, 2699 (2005);Search in Google Scholar
14. (c) doi:10.1021/ja0522783, S. J. Danishefsky, A. Endo. J. Am. Chem. Soc. 127, 8298 (2005);Search in Google Scholar
14. (d) doi:10.1021/ol0706051, T. Ling, V. R. Macherla, R. R. Manam, K. A. McArthur, B. C. M. Potts. Org. Lett. 9, 2289 (2007);Search in Google Scholar
14. (e) doi:10.1021/ol8016066, T. Fukuda, K. Sugiyama, S. Arima, Y. Harigaya, T. Nagamitsu, S. Omura. Org. Lett. 10, 4239 (2008);Search in Google Scholar
14. (f) doi:10.1039/b607109k, N. P. Mulholland, G. Pattenden, I. A. S. Walters. Org. Biomol. Chem. 4, 2845 (2006);Search in Google Scholar
14. (g) doi:10.1021/ol070616u, G. Ma, H. Nguyen, D. Romo. Org. Lett. 9, 2143 (2007);Search in Google Scholar
14. (h) doi:10.1016/j.tetlet.2006.11.087, V. Caubert, J. Masse, P. Retailleau, N. Langlois. Tetrahedron Lett. 48, 381 (2007);Search in Google Scholar
14. (i) doi:10.1016/j.tet.2008.06.038, I. V. Margalef, L. Rupnicki, H. W. Lam. Tetrahedron 64, 7896 (2008).Search in Google Scholar
15. J. A. Marshall. J. Org. Chem. 72, 8153 (2007) and refs. therein.10.1021/jo070787cSearch in Google Scholar
16. For example, the exo olefin instantaneously isomerized to the conjugated position under methanolytic conditions using K2CO3.Search in Google Scholar
17. doi:10.1016/j.tetlet.2005.05.003, B. V. S. Reddy, L. R. Reddy, E. J. Corey. Tetrahedron Lett. 46, 4589 (2005).Search in Google Scholar
18. (a) doi:10.1016/S0040-4039(00)98515-0, T. Mori, K. Takahashi, M. Kashiwabara, D. Uemura. Tetrahedron Lett. 26, 1073 (1985);Search in Google Scholar
18. (b) doi:10.1016/S0040-4039(00)98516-2, K. Takahashi, M. Kawabata, D. Uemura. Tetrahedron Lett. 26, 1077 (1985).Search in Google Scholar
19. doi:10.2174/1570163043334974, For review: M. G. Moloney, P. C. Trippier, M. Yaqoob, A. Wang. Curr. Drug Discov. Technol. 1, 181 (2004).Search in Google Scholar
20. (a) doi:10.1021/ol062705x, T. J. Donohoe, J. Y. K. Chiu, R. E. Thomas. Org. Lett. 9, 421 (2007);Search in Google Scholar
20. (b) N. J. Bennet, J. C. Prodger, G. Pattenden. Tetrahedron 63, 6216 (2007) and refs. therein.10.1016/j.tet.2007.03.043Search in Google Scholar
21. doi:10.1021/ja00166a072, A. S. Kende, K. Kawamura, R. J. DeVita. J. Am. Chem. Soc. 112, 4070 (1990).Search in Google Scholar
22. The NOESY spectrum was taken in [D8]THF/D2O (3:1) which was the same solvent system as that employed for the osmylation.Search in Google Scholar
23. Conformer 44 was suggested to be the energetically most stable by molecular mechanics calculations (MMFF, Macro Model 8.5).Search in Google Scholar
24. doi:10.1246/cl.1983.835, T. Fujisawa, T. Mori, T. Sato. Chem. Lett. 835 (1983).Search in Google Scholar
25. doi:10.1021/ja002377a, J. S. Panek, P. Liu. J. Am. Chem. Soc. 122, 11090 (2000).Search in Google Scholar
26. doi:10.1021/ol990967b, N. Henaff, A. Whiting. Org. Lett. 1, 1137 (1999).Search in Google Scholar
27. Y. Watanabe. WO 2003006422.Search in Google Scholar
28. (a) doi:10.1021/jo971410h, C. M. Shafer, T. F. Molinsky. J. Org. Chem. 63, 551 (1998);Search in Google Scholar
28. (b) doi:10.1016/j.tetlet.2003.08.044, J. P. Marino, H. N. Nguyen. Tetrahedron Lett. 44, 7395 (2003).Search in Google Scholar
© 2013 Walter de Gruyter GmbH, Berlin/Boston
