Formation of nine-membered lactams by oxidative ring expansion of 4- hydroxyhydroindoles: A biomimetic approach toward the tuberostemonone ring system?

Journal of Organic Chemistry

Volumn 64, Issue 13, 1999, Pages 4576-4577

  Wipf, Peter ^a   Li, Wenjie ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; INDOLE DERIVATIVE; IODOBENZENE; KETONE; LACTAM; OXOTUBEROSTEMONINE; PARVISTEMONINE; PLANT EXTRACT; STEMONINE; TUBEROSTEMONINE; UNCLASSIFIED DRUG;

ARTICLE; BRONCHITIS; CATALYSIS; CRYSTALLOGRAPHY; CYCLIZATION; DEGRADATION; METHODOLOGY; OXIDATION; OXYGENATION; SPECTROSCOPY;

EID: 0033603484     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9905064     Document Type: Article

References (28)

1. (a) Götz, M.; Strunz, G. M. Tuberostemonine and related compounds. Chemistry of the Stemona alkaloids. In Alkaloids; Wiesner, K., Ed.; MTP International Review of Sciences, Organic Chemistry, Series One; Butterworths: London, 1973; Vol. 9, pp 143-160.
2. (b) Tang, W.; Eisenbrand, G. Chinese Drugs of Plant Origin. Chemistry, Pharmacology, and Use in Traditional and Modern Medicine; Springer: Berlin, 1992; pp 957-961.
3. (a) Xu, R. S.; Lu, Y. J.; Chu, J. H.; Iwashita, T.; Naoki, H.; Naya, Y.; Nakanishi, K. Tetrahedron 1982, 38, 2667.
4. (b) Lin, W.; Ye, Y.; Xu, R. J. Nat. Prod. 1992, 55, 571.
5. (c) Lin, W. H.; Ma, L.; Cai, M. S.; Barnes, R. A. Phytochemistry 1984, 36, 1333 and references therein.
6. Croomine: (a) Williams, D. R.; Brown, D. L.; Benbow, J. W. J. Am. Chem. Soc. 1989, 111, 1923. (b) Martin, S. F.; Barr, K. J. J. Am. Chem. Soc. 1996, 118, 3299 . Stenine: (c) Chen, C. Y.; Hart, D. J. J. Org. Chem. 1993, 58, 3840. (d) Wipf, P.; Kim, Y.; Goldstein, D. M. J. Am. Chem. Soc. 1895, 177, 11106. (e) Morimoto, Y.; Iwahashi, M.; Nishida, K.; Hayashi, Y.; Shirahama, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 904. Stemoamide: (f) Williams, D. R.; Reddy, J. P.; Amato, G. S. Tetrahedron Lett. 1994, 35, 6417. (g) Kinoshita, A.; Mori, M. J. Org. Chem. 1996, 61, 8356. (h) Jacobi, P. A.; Lee, K. J. Am. Chem. Soc. 1997, 119, 3409.
7. Croomine: (a) Williams, D. R.; Brown, D. L.; Benbow, J. W. J. Am. Chem. Soc. 1989, 111, 1923. (b) Martin, S. F.; Barr, K. J. J. Am. Chem. Soc. 1996, 118, 3299 . Stenine: (c) Chen, C. Y.; Hart, D. J. J. Org. Chem. 1993, 58, 3840. (d) Wipf, P.; Kim, Y.; Goldstein, D. M. J. Am. Chem. Soc. 1895, 177, 11106. (e) Morimoto, Y.; Iwahashi, M.; Nishida, K.; Hayashi, Y.; Shirahama, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 904. Stemoamide: (f) Williams, D. R.; Reddy, J. P.; Amato, G. S. Tetrahedron Lett. 1994, 35, 6417. (g) Kinoshita, A.; Mori, M. J. Org. Chem. 1996, 61, 8356. (h) Jacobi, P. A.; Lee, K. J. Am. Chem. Soc. 1997, 119, 3409.
8. Croomine: (a) Williams, D. R.; Brown, D. L.; Benbow, J. W. J. Am. Chem. Soc. 1989, 111, 1923. (b) Martin, S. F.; Barr, K. J. J. Am. Chem. Soc. 1996, 118, 3299 . Stenine: (c) Chen, C. Y.; Hart, D. J. J. Org. Chem. 1993, 58, 3840. (d) Wipf, P.; Kim, Y.; Goldstein, D. M. J. Am. Chem. Soc. 1895, 177, 11106. (e) Morimoto, Y.; Iwahashi, M.; Nishida, K.; Hayashi, Y.; Shirahama, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 904. Stemoamide: (f) Williams, D. R.; Reddy, J. P.; Amato, G. S. Tetrahedron Lett. 1994, 35, 6417. (g) Kinoshita, A.; Mori, M. J. Org. Chem. 1996, 61, 8356. (h) Jacobi, P. A.; Lee, K. J. Am. Chem. Soc. 1997, 119, 3409.
9. Croomine: (a) Williams, D. R.; Brown, D. L.; Benbow, J. W. J. Am. Chem. Soc. 1989, 111, 1923. (b) Martin, S. F.; Barr, K. J. J. Am. Chem. Soc. 1996, 118, 3299 . Stenine: (c) Chen, C. Y.; Hart, D. J. J. Org. Chem. 1993, 58, 3840. (d) Wipf, P.; Kim, Y.; Goldstein, D. M. J. Am. Chem. Soc. 1895, 177, 11106. (e) Morimoto, Y.; Iwahashi, M.; Nishida, K.; Hayashi, Y.; Shirahama, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 904. Stemoamide: (f) Williams, D. R.; Reddy, J. P.; Amato, G. S. Tetrahedron Lett. 1994, 35, 6417. (g) Kinoshita, A.; Mori, M. J. Org. Chem. 1996, 61, 8356. (h) Jacobi, P. A.; Lee, K. J. Am. Chem. Soc. 1997, 119, 3409.
10. Croomine: (a) Williams, D. R.; Brown, D. L.; Benbow, J. W. J. Am. Chem. Soc. 1989, 111, 1923. (b) Martin, S. F.; Barr, K. J. J. Am. Chem. Soc. 1996, 118, 3299 . Stenine: (c) Chen, C. Y.; Hart, D. J. J. Org. Chem. 1993, 58, 3840. (d) Wipf, P.; Kim, Y.; Goldstein, D. M. J. Am. Chem. Soc. 1895, 177, 11106. (e) Morimoto, Y.; Iwahashi, M.; Nishida, K.; Hayashi, Y.; Shirahama, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 904. Stemoamide: (f) Williams, D. R.; Reddy, J. P.; Amato, G. S. Tetrahedron Lett. 1994, 35, 6417. (g) Kinoshita, A.; Mori, M. J. Org. Chem. 1996, 61, 8356. (h) Jacobi, P. A.; Lee, K. J. Am. Chem. Soc. 1997, 119, 3409.
11. Croomine: (a) Williams, D. R.; Brown, D. L.; Benbow, J. W. J. Am. Chem. Soc. 1989, 111, 1923. (b) Martin, S. F.; Barr, K. J. J. Am. Chem. Soc. 1996, 118, 3299 . Stenine: (c) Chen, C. Y.; Hart, D. J. J. Org. Chem. 1993, 58, 3840. (d) Wipf, P.; Kim, Y.; Goldstein, D. M. J. Am. Chem. Soc. 1895, 177, 11106. (e) Morimoto, Y.; Iwahashi, M.; Nishida, K.; Hayashi, Y.; Shirahama, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 904. Stemoamide: (f) Williams, D. R.; Reddy, J. P.; Amato, G. S. Tetrahedron Lett. 1994, 35, 6417. (g) Kinoshita, A.; Mori, M. J. Org. Chem. 1996, 61, 8356. (h) Jacobi, P. A.; Lee, K. J. Am. Chem. Soc. 1997, 119, 3409.
12. Croomine: (a) Williams, D. R.; Brown, D. L.; Benbow, J. W. J. Am. Chem. Soc. 1989, 111, 1923. (b) Martin, S. F.; Barr, K. J. J. Am. Chem. Soc. 1996, 118, 3299 . Stenine: (c) Chen, C. Y.; Hart, D. J. J. Org. Chem. 1993, 58, 3840. (d) Wipf, P.; Kim, Y.; Goldstein, D. M. J. Am. Chem. Soc. 1895, 177, 11106. (e) Morimoto, Y.; Iwahashi, M.; Nishida, K.; Hayashi, Y.; Shirahama, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 904. Stemoamide: (f) Williams, D. R.; Reddy, J. P.; Amato, G. S. Tetrahedron Lett. 1994, 35, 6417. (g) Kinoshita, A.; Mori, M. J. Org. Chem. 1996, 61, 8356. (h) Jacobi, P. A.; Lee, K. J. Am. Chem. Soc. 1997, 119, 3409.
13. Croomine: (a) Williams, D. R.; Brown, D. L.; Benbow, J. W. J. Am. Chem. Soc. 1989, 111, 1923. (b) Martin, S. F.; Barr, K. J. J. Am. Chem. Soc. 1996, 118, 3299 . Stenine: (c) Chen, C. Y.; Hart, D. J. J. Org. Chem. 1993, 58, 3840. (d) Wipf, P.; Kim, Y.; Goldstein, D. M. J. Am. Chem. Soc. 1895, 177, 11106. (e) Morimoto, Y.; Iwahashi, M.; Nishida, K.; Hayashi, Y.; Shirahama, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 904. Stemoamide: (f) Williams, D. R.; Reddy, J. P.; Amato, G. S. Tetrahedron Lett. 1994, 35, 6417. (g) Kinoshita, A.; Mori, M. J. Org. Chem. 1996, 61, 8356. (h) Jacobi, P. A.; Lee, K. J. Am. Chem. Soc. 1997, 119, 3409.
14. Goldstein, D. M.; Wipf, P. Tetrahedron Lett. 1996, 37, 739.
15. Lin, W.; Xu, R.; Wang, R.; Mak, T. C. W. J. Crystallogr. Spectrosc. Res. 1991, 21, 189.
16. Cheng, D.; Guo, J.; Chu, T. T.; Roeder, E. J. Nat. Prod. 1988, 52, 202.
17. Lin, W.; Yin, B.; Tang, Z.; Xu, R.; Zhong, Q. Huaxue Xuebao 1990, 48, 811.
18. Goetz, M.; Boegri, T.; Gray, A. H.; Strunz, G. M. Tetrahedron 1968, 24, 2631.
19. Edwards, O. E.; Feniak, G.; Handa, K. L. Can. J. Chem. 1962, 40, 455.
20. Wipf, P.; Kim, Y. Tetrahedron Lett. 1992, 33, 5477.
21. Swiss, K. A.; Hinkley, W.; Maryanoff, C. A.; Liotta, D. C. Synthesis 1992, 127.
22. (a) Concepcion, J. I.; Francisco, C. G.; Hernandez, R.; Salazar, J. A.; Suarez, E. Tetrahedron Lett. 1984, 25, 1953.
23. (b) Ochiai, M.; Iwaki, S.; Ukita, T.; Nagao, Y. Chem. Lett. 1987, 133.
24. (c) Hernandez, R.; Melian, D.; Prange, D.; Suarez, E. Heterocyles 1995, 41, 439.
25. 2/hexanes, an X-ray structure analysis of the major β-epimer of 4 confirmed the structure assignment for the fragmentation process.
26. Grieco, P. A.; Oguri, T.; Yokoyama, Y. Tetrahedron Lett. 1978, 19, 419.
27. For the fragmentation of a peracid-iminium ion adduct with pyridine to give a β-lactam, see: Wasserman, H. H.; Tremper, A. W. Tetrahedron Lett. 1977, 18, 1449.
28. Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., and Paquette, L. A., Eds.; Pergamon: Oxford, U.K., 1991; Vol. 5, pp 827-874.