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http://dx.doi.org/10.5012/bkcs.2009.30.3.691

A Convenient Synthesis of Polycyclic γ-Lactams via Pauson-Khand Reaction  

Kang, Seok-Won (Department of Chemistry, Konkuk University)
Kim, Yong-Hoon (Department of Chemistry, Konkuk University)
Kim, Hea-Jeong (Department of Chemistry, Konkuk University)
Lee, Joo-Hee (Department of Chemistry, Konkuk University)
Kim, Sung-Hoon (Department of Chemistry, Konkuk University)
Publication Information
Bulletin of the Korean Chemical Society / v.30, no.3, 2009 , pp. 691-694 More about this Journal
Abstract
Pauson-Khand reaction of hydroxyenynes with $Co_2(CO)_8$ in the presence of N-methylmorpholine N-oxide or trimethylamine N-oxide as a promoter produced polycyclic $gamma$-lactams as single stereoisomers in moderate to excellent yield. These are the first examples of an intramolecular Pauson-Khand reaction on a hydroxyenyne system tethered to a three- and four-membered ring as new skeletons with 5,6,5 fused ring systems.
Keywords
Polycyclic $\gamma$-lactams; Pauson-Khand reaction; 5,6,5 Fused ring systems; $Co_{2}(CO)_{8}$;
Citations & Related Records
Times Cited By KSCI : 1  (Citation Analysis)
Times Cited By Web Of Science : 0  (Related Records In Web of Science)
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1 Kang, S. W.; Heo, E. Y.; Jun, J. G.; Kim, S. H. Bull. Korean Chem. Soc. 2004, 25, 1924   DOI   ScienceOn
2 CAChe, Work System Pro Version 5.02; Fujitsu Ltd., Oxford Molecular Group Inc.: 2000-2002
3 Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision C.02; Gaussian, Inc.: Wallingford, CT, 2004
4 Balasubramanian, M.; Keay, J. G. Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996; Vol. 5, p 245
5 Lewis, J. R. Nat. Prod. Rep. 1994, 11, 329   DOI   ScienceOn
6 Kuehne, M. E.; Matsko, T. H.; Bohnert, J. C.; Motyka, L.; Oliver-Smith, D. J. Org. Chem. 1981, 46, 2002   DOI   ScienceOn
7 Kuehne, M. E.; Earley, W. G. Tetrahedron 1983, 39, 3707   DOI   ScienceOn
8 Rigby, J. H.; Laurent, S.; Cavezza, A.; Heeg, M. J. J. Org. Chem. 1998, 63, 5587   DOI   ScienceOn
9 Kraus, G. A.; Thomas, P. J.; Bougie, D.; Chen, L. J. Org. Chem. 1990, 55, 1624   DOI   ScienceOn
10 Gribble, G. W. Comprehensive Heterocyclic Chemistry II;Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996; Vol. 2, p 207
11 Martin, S. F. In The Alkaloids; Brossi, A., Ed.; Academic: New York, 1987; Vol. 30, p 251
12 Pauson, P. L. Tetrahedron 1985, 41, 5855-5860   DOI   ScienceOn
13 Nkiliza, J.; Vercauteren, J. Tetrahedron Lett. 1991, 32, 1787   DOI   ScienceOn
14 Overman, L. E.; Sugai, S. Helv. Chim. Acta 1985, 68, 745   DOI
15 Rawal, V. H.; Michoud, C.; Monestel, R. F. J. Am. Chem. Soc. 1993, 46, 3030   DOI   ScienceOn
16 Kuehne, M. E.; Brook, C. S.; Xu, F.; Parsons, R. Pure Appl. Chem. 1994, 66, 2095   DOI   ScienceOn
17 Overman, L. E.; Sworin, M.; Burk, R. M. J. Org. Chem. 1983, 48, 2685   DOI
18 Overman, L. E.; Robertson, G.; Robichaud, A. J. J. Org. Chem. 1989, 54, 1236   DOI   ScienceOn
19 Gallagher, T.; Magnus, P.; Huffman, J. C. J. Am. Chem. Soc. 1983, 105, 4750   DOI   ScienceOn
20 Magnus, P.; Gallagher, T.; Brown, P.; Pappalardo, P. Acc. Chem. Res. 1984, 17, 35   DOI   ScienceOn
21 Rigby, J. H.; Qabar, M. H. J. Org. Chem. 1993, 58, 4473   DOI   ScienceOn
22 Rigby, J. H.; Qabar, M.; Ahmed, G.; Hughes, R. C. Tetrahedron 1993, 49, 10219   DOI   ScienceOn
23 Rigby, J. H.; Hughes, R. C.; Heeg, M. J. J. Am. Chem. Soc. 1995, 117, 7834   DOI   ScienceOn
24 Rigby, J. H.; Mateo, M. E. Tetrahedron 1996, 52, 10569   DOI   ScienceOn
25 Sole, D.; Bonjoch, J. Tetrahedron Lett. 1991, 32, 5183   DOI   ScienceOn
26 Schultz, A. G.; Holoboski, M. A.; Smyth, M. S. J. Am. Chem. Soc. 1996, 118, 6210   DOI   ScienceOn
27 Bonjoch, J.; Sole, D.; Bosch, J. J. Am. Chem. Soc. 1993, 115, 2064   DOI   ScienceOn
28 Schultz, A. G.; Holoboski, M. A.; Smyth, M. S. J. Am. Chem. Soc. 1993, 115, 7904   DOI   ScienceOn
29 Guzzo, P. R.; Nowak, D. M. J. Org. Chem. 1995, 60, 8044   DOI   ScienceOn
30 Pearson, W. H.; Postich, M. J. J. Org. Chem. 1994, 59, 5662   DOI   ScienceOn
31 Padwa, A.; Price, A. T. J. Org. Chem. 1995, 60, 6258   DOI   ScienceOn
32 Takano, S.; Inomata, K.; Ogasawara, K. Chem. Lett. 1992, 443   DOI   ScienceOn
33 Uesaka, N.; Saitoh, F.; Mori, M.; Shibasaki, M.; Okamura, K.; Date, T. J. Org. Chem. 1994, 59, 5633   DOI   ScienceOn
34 Mori, M.; Kuroda, S.; Zhang, C.; Sato, Y. J. Org. Chem. 1997, 62, 3263   DOI   ScienceOn
35 In Comprehensive Organic Synthesis; Shore, N. E., Trost, B. M., Fleming, I., Pattanden, G., Eds.; Pergamon: Oxford, 1991; Vol. 5, pp 1037-1064
36 Schore, N. E. Organic Reactions 1991, 40, 1-90   DOI   ScienceOn
37 Ching, Y. K. Coord. Chem. Rev. 1999, 188, 297–341   DOI   ScienceOn
38 Schafer, W.; Friebe, W.-G.; Leinert, H.; Mertens, A.; Poll, T.; von der Saal, W.; Zilch, H.; Nuber, B.; Ziegler, M. L. J. Med. Chem. 1993, 36, 762   DOI   ScienceOn
39 Brummond, K. M.; Kent, J. L. Tetrahedron 2000, 56, 3263-3283   DOI   ScienceOn
40 Mertens, A.; Zilch, H.; Konig, B.; Schafer, W.; Poll, T.; Kampe, W.; Seidel, H.; Leser, U.; Leinert, H. J. Med. Chem.1993, 36, 2526   DOI   ScienceOn
41 Allin, S. M.; Northfield, C. J.; Page, M. I.; Slawin, A. M. Z. Tetrahedron Lett. 1997, 38, 3627   DOI   ScienceOn
42 Allin, S. M.; Northfield, C. J.; Page, M. I.; Slawin, A. M. Z. Tetrahedron Lett. 1999, 40, 141   DOI   ScienceOn
43 Allin, S. M.; Northfield, C. J.; Page, M. I.; Slawin, A. M. Z. Tetrahedron Lett. 1999, 40, 143   DOI   ScienceOn
44 Allin, S. M.; Hodkinson, C. C.; Taj, N. Synlett 1996, 781   DOI   ScienceOn
45 Kang, S. W.; Kim, Y. H.; Kim, S. H. Bull. Korean Chem. Soc. 2008, 29, 755   DOI   ScienceOn
46 Kim, S. H.; Han, E. Y. Tetrahedron Lett. 2000, 41, 6479   DOI   ScienceOn
47 Marson, C. M.; Khan, A.; Porter, R. A. J. Org. Chem. 2001, 66, 4771   DOI   ScienceOn
48 Butler, D. N.; Shang, M.; Warrener, R. N. Tetrahedron Lett. 2000, 41, 5985   DOI   ScienceOn
49 Jeffs, P. W. In The Alkaloids; Rodrigo, R. G. A., Ed.; Academic: New York, 1981; Vol. 19, pp 1-80   DOI
50 Jeong, N.; Chung, Y. K.; Lee, B. Y.; Lee, S. H.; Yoo, S. E. Synlett 1991, 204