Enantiopure N-Acyldihydropyridones as Synthetic Intermediates: Asymmetric Synthesis of (-)-Septicine and (-)-Tylophorine

Journal of Organic Chemistry

Volumn 62, Issue 21, 1997, Pages 7435-7438

  Comins, Daniel L ^a   Chen, Xinghai ^a   Morgan, Lawrence A ^a  

^a NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542396379     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9711495     Document Type: Article

References (44)

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2. Reviews: (a) Gellert, E. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; John Wiley & Sons: New York, 1987; Vol. 5, p 55. (b) Suffness, M.; Cordell, G. A. In The Alkaloids; Brossi, A., Ed.; Academic Press: Orlando, FL, 1985; Vol. 25, Chapter 1, pp 3-355.
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12. Syntheses of (±)-septicine: (a) Govindachari, T. R.; Viswanethan, N. Tetrahedron 1970, 26, 715. (b) Stevens, R. V.; Luh, Y. Tetrehedron Lett. 1977, 979. (c) Iwashita, T.; Suzuki, M.; Kusumi, T.; Kakisawa, H. Chem. Lett. 1980, 383. (d) Cragg, J. E.; Herbert, R. B.; Jackson, F. B.; Moody, C. J.; Nicolson, I. T. J. Chem. Soc., Perkin Trans. 1 1982, 2477. (e) Iida, H.; Watanabe, Y.; Tanaka, M.; Kibayashi, C. J. Org. Chem. 1984, 49, 2412. (f) Comins, D. L.; Morgan, L. A., Tetrahedron Lett. 1991, 32, 5919. (g) Verxa, B. R.; Yang, K.; Moore, H. W. Tetrahedron 1994, 50, 6173. (h) Ciufolini, M. A.; Roschangar, F. J. Am. Chem. Soc. 1996, 118, 12082.
13. Syntheses of (±)-septicine: (a) Govindachari, T. R.; Viswanethan, N. Tetrahedron 1970, 26, 715. (b) Stevens, R. V.; Luh, Y. Tetrehedron Lett. 1977, 979. (c) Iwashita, T.; Suzuki, M.; Kusumi, T.; Kakisawa, H. Chem. Lett. 1980, 383. (d) Cragg, J. E.; Herbert, R. B.; Jackson, F. B.; Moody, C. J.; Nicolson, I. T. J. Chem. Soc., Perkin Trans. 1 1982, 2477. (e) Iida, H.; Watanabe, Y.; Tanaka, M.; Kibayashi, C. J. Org. Chem. 1984, 49, 2412. (f) Comins, D. L.; Morgan, L. A., Tetrahedron Lett. 1991, 32, 5919. (g) Verxa, B. R.; Yang, K.; Moore, H. W. Tetrahedron 1994, 50, 6173. (h) Ciufolini, M. A.; Roschangar, F. J. Am. Chem. Soc. 1996, 118, 12082.
14. Syntheses of (±)-septicine: (a) Govindachari, T. R.; Viswanethan, N. Tetrahedron 1970, 26, 715. (b) Stevens, R. V.; Luh, Y. Tetrehedron Lett. 1977, 979. (c) Iwashita, T.; Suzuki, M.; Kusumi, T.; Kakisawa, H. Chem. Lett. 1980, 383. (d) Cragg, J. E.; Herbert, R. B.; Jackson, F. B.; Moody, C. J.; Nicolson, I. T. J. Chem. Soc., Perkin Trans. 1 1982, 2477. (e) Iida, H.; Watanabe, Y.; Tanaka, M.; Kibayashi, C. J. Org. Chem. 1984, 49, 2412. (f) Comins, D. L.; Morgan, L. A., Tetrahedron Lett. 1991, 32, 5919. (g) Verxa, B. R.; Yang, K.; Moore, H. W. Tetrahedron 1994, 50, 6173. (h) Ciufolini, M. A.; Roschangar, F. J. Am. Chem. Soc. 1996, 118, 12082.
15. Syntheses of (±)-septicine: (a) Govindachari, T. R.; Viswanethan, N. Tetrahedron 1970, 26, 715. (b) Stevens, R. V.; Luh, Y. Tetrehedron Lett. 1977, 979. (c) Iwashita, T.; Suzuki, M.; Kusumi, T.; Kakisawa, H. Chem. Lett. 1980, 383. (d) Cragg, J. E.; Herbert, R. B.; Jackson, F. B.; Moody, C. J.; Nicolson, I. T. J. Chem. Soc., Perkin Trans. 1 1982, 2477. (e) Iida, H.; Watanabe, Y.; Tanaka, M.; Kibayashi, C. J. Org. Chem. 1984, 49, 2412. (f) Comins, D. L.; Morgan, L. A., Tetrahedron Lett. 1991, 32, 5919. (g) Verxa, B. R.; Yang, K.; Moore, H. W. Tetrahedron 1994, 50, 6173. (h) Ciufolini, M. A.; Roschangar, F. J. Am. Chem. Soc. 1996, 118, 12082.
16. Syntheses of (±)-septicine: (a) Govindachari, T. R.; Viswanethan, N. Tetrahedron 1970, 26, 715. (b) Stevens, R. V.; Luh, Y. Tetrehedron Lett. 1977, 979. (c) Iwashita, T.; Suzuki, M.; Kusumi, T.; Kakisawa, H. Chem. Lett. 1980, 383. (d) Cragg, J. E.; Herbert, R. B.; Jackson, F. B.; Moody, C. J.; Nicolson, I. T. J. Chem. Soc., Perkin Trans. 1 1982, 2477. (e) Iida, H.; Watanabe, Y.; Tanaka, M.; Kibayashi, C. J. Org. Chem. 1984, 49, 2412. (f) Comins, D. L.; Morgan, L. A., Tetrahedron Lett. 1991, 32, 5919. (g) Verxa, B. R.; Yang, K.; Moore, H. W. Tetrahedron 1994, 50, 6173. (h) Ciufolini, M. A.; Roschangar, F. J. Am. Chem. Soc. 1996, 118, 12082.
17. Syntheses of (±)-septicine: (a) Govindachari, T. R.; Viswanethan, N. Tetrahedron 1970, 26, 715. (b) Stevens, R. V.; Luh, Y. Tetrehedron Lett. 1977, 979. (c) Iwashita, T.; Suzuki, M.; Kusumi, T.; Kakisawa, H. Chem. Lett. 1980, 383. (d) Cragg, J. E.; Herbert, R. B.; Jackson, F. B.; Moody, C. J.; Nicolson, I. T. J. Chem. Soc., Perkin Trans. 1 1982, 2477. (e) Iida, H.; Watanabe, Y.; Tanaka, M.; Kibayashi, C. J. Org. Chem. 1984, 49, 2412. (f) Comins, D. L.; Morgan, L. A., Tetrahedron Lett. 1991, 32, 5919. (g) Verxa, B. R.; Yang, K.; Moore, H. W. Tetrahedron 1994, 50, 6173. (h) Ciufolini, M. A.; Roschangar, F. J. Am. Chem. Soc. 1996, 118, 12082.
18. Syntheses of (±)-septicine: (a) Govindachari, T. R.; Viswanethan, N. Tetrahedron 1970, 26, 715. (b) Stevens, R. V.; Luh, Y. Tetrehedron Lett. 1977, 979. (c) Iwashita, T.; Suzuki, M.; Kusumi, T.; Kakisawa, H. Chem. Lett. 1980, 383. (d) Cragg, J. E.; Herbert, R. B.; Jackson, F. B.; Moody, C. J.; Nicolson, I. T. J. Chem. Soc., Perkin Trans. 1 1982, 2477. (e) Iida, H.; Watanabe, Y.; Tanaka, M.; Kibayashi, C. J. Org. Chem. 1984, 49, 2412. (f) Comins, D. L.; Morgan, L. A., Tetrahedron Lett. 1991, 32, 5919. (g) Verxa, B. R.; Yang, K.; Moore, H. W. Tetrahedron 1994, 50, 6173. (h) Ciufolini, M. A.; Roschangar, F. J. Am. Chem. Soc. 1996, 118, 12082.
19. Syntheses of (±)-septicine: (a) Govindachari, T. R.; Viswanethan, N. Tetrahedron 1970, 26, 715. (b) Stevens, R. V.; Luh, Y. Tetrehedron Lett. 1977, 979. (c) Iwashita, T.; Suzuki, M.; Kusumi, T.; Kakisawa, H. Chem. Lett. 1980, 383. (d) Cragg, J. E.; Herbert, R. B.; Jackson, F. B.; Moody, C. J.; Nicolson, I. T. J. Chem. Soc., Perkin Trans. 1 1982, 2477. (e) Iida, H.; Watanabe, Y.; Tanaka, M.; Kibayashi, C. J. Org. Chem. 1984, 49, 2412. (f) Comins, D. L.; Morgan, L. A., Tetrahedron Lett. 1991, 32, 5919. (g) Verxa, B. R.; Yang, K.; Moore, H. W. Tetrahedron 1994, 50, 6173. (h) Ciufolini, M. A.; Roschangar, F. J. Am. Chem. Soc. 1996, 118, 12082.
20. Syntheses of (±)-tylophorine: (a) Govindachari, T. R.; Laksmikantham, M. V.; Rajadurai, S. Tetrahedron 1961, 14, 284-287. (b) Herbert, R. B.; Moody, C. J. J. Chem. Soc. D 1970, 2, 121. (c) Chauncy, B.; Gellert, E. Aust. J. Chem. 1970, 23, 2503. (d) Liepa, A. J.; Summons, R. E. J. Chem. Soc., Chem. Commun. 1977, 826. (e) Weinreb, S. M.; Khatri, N. A.; Shringarpure, J. J. Am. Chem. Soc. 1979, 101, 5073. (f) Mangla, V. K.; Bhakuni, D. S. Tetrahedron 1980, 36, 2489. (g) Khatri, N. A.; Schmitthenner, H. F.; Shringarpure, J.; Weinreb, S. M. J. Am. Chem. Soc. 1981, 103, 6387. (h) Cragg, J. E.; Herbert, R. B.; Jackson, F. B.; Moody, C. J.; Nicholson, I. T. J. Chem. Soc., Perkin Trans. 1 1982, 2477. (i) Iida, H.; Tanaka, M.; Kibayashi, C. J. Chem. Soc., Chem. Commun. 1983, 271. (j) Iida, H.; Watanabe, Y.; Tanaka, M.; Kibayashi, C. J. Org. Chem. 1984, 49, 2412. (k) Ihara, M.; Tsuruta, M.; Fukumoto, K.; Kametani, T. J. Chem. Soc., Chem. Commun. 1985, 1159. (l) Comins, D. L.; Morgan, L. A. Tetrahedron Lett. 1991, 32, 5919. (m) Pearson, W. H.; Walavalkar, R. Tetrahedron Lett. 1994, 50, 12293. (n) Reference 7h.
21. Syntheses of (±)-tylophorine: (a) Govindachari, T. R.; Laksmikantham, M. V.; Rajadurai, S. Tetrahedron 1961, 14, 284-287. (b) Herbert, R. B.; Moody, C. J. J. Chem. Soc. D 1970, 2, 121. (c) Chauncy, B.; Gellert, E. Aust. J. Chem. 1970, 23, 2503. (d) Liepa, A. J.; Summons, R. E. J. Chem. Soc., Chem. Commun. 1977, 826. (e) Weinreb, S. M.; Khatri, N. A.; Shringarpure, J. J. Am. Chem. Soc. 1979, 101, 5073. (f) Mangla, V. K.; Bhakuni, D. S. Tetrahedron 1980, 36, 2489. (g) Khatri, N. A.; Schmitthenner, H. F.; Shringarpure, J.; Weinreb, S. M. J. Am. Chem. Soc. 1981, 103, 6387. (h) Cragg, J. E.; Herbert, R. B.; Jackson, F. B.; Moody, C. J.; Nicholson, I. T. J. Chem. Soc., Perkin Trans. 1 1982, 2477. (i) Iida, H.; Tanaka, M.; Kibayashi, C. J. Chem. Soc., Chem. Commun. 1983, 271. (j) Iida, H.; Watanabe, Y.; Tanaka, M.; Kibayashi, C. J. Org. Chem. 1984, 49, 2412. (k) Ihara, M.; Tsuruta, M.; Fukumoto, K.; Kametani, T. J. Chem. Soc., Chem. Commun. 1985, 1159. (l) Comins, D. L.; Morgan, L. A. Tetrahedron Lett. 1991, 32, 5919. (m) Pearson, W. H.; Walavalkar, R. Tetrahedron Lett. 1994, 50, 12293. (n) Reference 7h.
22. Syntheses of (±)-tylophorine: (a) Govindachari, T. R.; Laksmikantham, M. V.; Rajadurai, S. Tetrahedron 1961, 14, 284-287. (b) Herbert, R. B.; Moody, C. J. J. Chem. Soc. D 1970, 2, 121. (c) Chauncy, B.; Gellert, E. Aust. J. Chem. 1970, 23, 2503. (d) Liepa, A. J.; Summons, R. E. J. Chem. Soc., Chem. Commun. 1977, 826. (e) Weinreb, S. M.; Khatri, N. A.; Shringarpure, J. J. Am. Chem. Soc. 1979, 101, 5073. (f) Mangla, V. K.; Bhakuni, D. S. Tetrahedron 1980, 36, 2489. (g) Khatri, N. A.; Schmitthenner, H. F.; Shringarpure, J.; Weinreb, S. M. J. Am. Chem. Soc. 1981, 103, 6387. (h) Cragg, J. E.; Herbert, R. B.; Jackson, F. B.; Moody, C. J.; Nicholson, I. T. J. Chem. Soc., Perkin Trans. 1 1982, 2477. (i) Iida, H.; Tanaka, M.; Kibayashi, C. J. Chem. Soc., Chem. Commun. 1983, 271. (j) Iida, H.; Watanabe, Y.; Tanaka, M.; Kibayashi, C. J. Org. Chem. 1984, 49, 2412. (k) Ihara, M.; Tsuruta, M.; Fukumoto, K.; Kametani, T. J. Chem. Soc., Chem. Commun. 1985, 1159. (l) Comins, D. L.; Morgan, L. A. Tetrahedron Lett. 1991, 32, 5919. (m) Pearson, W. H.; Walavalkar, R. Tetrahedron Lett. 1994, 50, 12293. (n) Reference 7h.
23. Syntheses of (±)-tylophorine: (a) Govindachari, T. R.; Laksmikantham, M. V.; Rajadurai, S. Tetrahedron 1961, 14, 284-287. (b) Herbert, R. B.; Moody, C. J. J. Chem. Soc. D 1970, 2, 121. (c) Chauncy, B.; Gellert, E. Aust. J. Chem. 1970, 23, 2503. (d) Liepa, A. J.; Summons, R. E. J. Chem. Soc., Chem. Commun. 1977, 826. (e) Weinreb, S. M.; Khatri, N. A.; Shringarpure, J. J. Am. Chem. Soc. 1979, 101, 5073. (f) Mangla, V. K.; Bhakuni, D. S. Tetrahedron 1980, 36, 2489. (g) Khatri, N. A.; Schmitthenner, H. F.; Shringarpure, J.; Weinreb, S. M. J. Am. Chem. Soc. 1981, 103, 6387. (h) Cragg, J. E.; Herbert, R. B.; Jackson, F. B.; Moody, C. J.; Nicholson, I. T. J. Chem. Soc., Perkin Trans. 1 1982, 2477. (i) Iida, H.; Tanaka, M.; Kibayashi, C. J. Chem. Soc., Chem. Commun. 1983, 271. (j) Iida, H.; Watanabe, Y.; Tanaka, M.; Kibayashi, C. J. Org. Chem. 1984, 49, 2412. (k) Ihara, M.; Tsuruta, M.; Fukumoto, K.; Kametani, T. J. Chem. Soc., Chem. Commun. 1985, 1159. (l) Comins, D. L.; Morgan, L. A. Tetrahedron Lett. 1991, 32, 5919. (m) Pearson, W. H.; Walavalkar, R. Tetrahedron Lett. 1994, 50, 12293. (n) Reference 7h.
24. Syntheses of (±)-tylophorine: (a) Govindachari, T. R.; Laksmikantham, M. V.; Rajadurai, S. Tetrahedron 1961, 14, 284-287. (b) Herbert, R. B.; Moody, C. J. J. Chem. Soc. D 1970, 2, 121. (c) Chauncy, B.; Gellert, E. Aust. J. Chem. 1970, 23, 2503. (d) Liepa, A. J.; Summons, R. E. J. Chem. Soc., Chem. Commun. 1977, 826. (e) Weinreb, S. M.; Khatri, N. A.; Shringarpure, J. J. Am. Chem. Soc. 1979, 101, 5073. (f) Mangla, V. K.; Bhakuni, D. S. Tetrahedron 1980, 36, 2489. (g) Khatri, N. A.; Schmitthenner, H. F.; Shringarpure, J.; Weinreb, S. M. J. Am. Chem. Soc. 1981, 103, 6387. (h) Cragg, J. E.; Herbert, R. B.; Jackson, F. B.; Moody, C. J.; Nicholson, I. T. J. Chem. Soc., Perkin Trans. 1 1982, 2477. (i) Iida, H.; Tanaka, M.; Kibayashi, C. J. Chem. Soc., Chem. Commun. 1983, 271. (j) Iida, H.; Watanabe, Y.; Tanaka, M.; Kibayashi, C. J. Org. Chem. 1984, 49, 2412. (k) Ihara, M.; Tsuruta, M.; Fukumoto, K.; Kametani, T. J. Chem. Soc., Chem. Commun. 1985, 1159. (l) Comins, D. L.; Morgan, L. A. Tetrahedron Lett. 1991, 32, 5919. (m) Pearson, W. H.; Walavalkar, R. Tetrahedron Lett. 1994, 50, 12293. (n) Reference 7h.
25. Syntheses of (±)-tylophorine: (a) Govindachari, T. R.; Laksmikantham, M. V.; Rajadurai, S. Tetrahedron 1961, 14, 284-287. (b) Herbert, R. B.; Moody, C. J. J. Chem. Soc. D 1970, 2, 121. (c) Chauncy, B.; Gellert, E. Aust. J. Chem. 1970, 23, 2503. (d) Liepa, A. J.; Summons, R. E. J. Chem. Soc., Chem. Commun. 1977, 826. (e) Weinreb, S. M.; Khatri, N. A.; Shringarpure, J. J. Am. Chem. Soc. 1979, 101, 5073. (f) Mangla, V. K.; Bhakuni, D. S. Tetrahedron 1980, 36, 2489. (g) Khatri, N. A.; Schmitthenner, H. F.; Shringarpure, J.; Weinreb, S. M. J. Am. Chem. Soc. 1981, 103, 6387. (h) Cragg, J. E.; Herbert, R. B.; Jackson, F. B.; Moody, C. J.; Nicholson, I. T. J. Chem. Soc., Perkin Trans. 1 1982, 2477. (i) Iida, H.; Tanaka, M.; Kibayashi, C. J. Chem. Soc., Chem. Commun. 1983, 271. (j) Iida, H.; Watanabe, Y.; Tanaka, M.; Kibayashi, C. J. Org. Chem. 1984, 49, 2412. (k) Ihara, M.; Tsuruta, M.; Fukumoto, K.; Kametani, T. J. Chem. Soc., Chem. Commun. 1985, 1159. (l) Comins, D. L.; Morgan, L. A. Tetrahedron Lett. 1991, 32, 5919. (m) Pearson, W. H.; Walavalkar, R. Tetrahedron Lett. 1994, 50, 12293. (n) Reference 7h.
26. Syntheses of (±)-tylophorine: (a) Govindachari, T. R.; Laksmikantham, M. V.; Rajadurai, S. Tetrahedron 1961, 14, 284-287. (b) Herbert, R. B.; Moody, C. J. J. Chem. Soc. D 1970, 2, 121. (c) Chauncy, B.; Gellert, E. Aust. J. Chem. 1970, 23, 2503. (d) Liepa, A. J.; Summons, R. E. J. Chem. Soc., Chem. Commun. 1977, 826. (e) Weinreb, S. M.; Khatri, N. A.; Shringarpure, J. J. Am. Chem. Soc. 1979, 101, 5073. (f) Mangla, V. K.; Bhakuni, D. S. Tetrahedron 1980, 36, 2489. (g) Khatri, N. A.; Schmitthenner, H. F.; Shringarpure, J.; Weinreb, S. M. J. Am. Chem. Soc. 1981, 103, 6387. (h) Cragg, J. E.; Herbert, R. B.; Jackson, F. B.; Moody, C. J.; Nicholson, I. T. J. Chem. Soc., Perkin Trans. 1 1982, 2477. (i) Iida, H.; Tanaka, M.; Kibayashi, C. J. Chem. Soc., Chem. Commun. 1983, 271. (j) Iida, H.; Watanabe, Y.; Tanaka, M.; Kibayashi, C. J. Org. Chem. 1984, 49, 2412. (k) Ihara, M.; Tsuruta, M.; Fukumoto, K.; Kametani, T. J. Chem. Soc., Chem. Commun. 1985, 1159. (l) Comins, D. L.; Morgan, L. A. Tetrahedron Lett. 1991, 32, 5919. (m) Pearson, W. H.; Walavalkar, R. Tetrahedron Lett. 1994, 50, 12293. (n) Reference 7h.
27. Syntheses of (±)-tylophorine: (a) Govindachari, T. R.; Laksmikantham, M. V.; Rajadurai, S. Tetrahedron 1961, 14, 284-287. (b) Herbert, R. B.; Moody, C. J. J. Chem. Soc. D 1970, 2, 121. (c) Chauncy, B.; Gellert, E. Aust. J. Chem. 1970, 23, 2503. (d) Liepa, A. J.; Summons, R. E. J. Chem. Soc., Chem. Commun. 1977, 826. (e) Weinreb, S. M.; Khatri, N. A.; Shringarpure, J. J. Am. Chem. Soc. 1979, 101, 5073. (f) Mangla, V. K.; Bhakuni, D. S. Tetrahedron 1980, 36, 2489. (g) Khatri, N. A.; Schmitthenner, H. F.; Shringarpure, J.; Weinreb, S. M. J. Am. Chem. Soc. 1981, 103, 6387. (h) Cragg, J. E.; Herbert, R. B.; Jackson, F. B.; Moody, C. J.; Nicholson, I. T. J. Chem. Soc., Perkin Trans. 1 1982, 2477. (i) Iida, H.; Tanaka, M.; Kibayashi, C. J. Chem. Soc., Chem. Commun. 1983, 271. (j) Iida, H.; Watanabe, Y.; Tanaka, M.; Kibayashi, C. J. Org. Chem. 1984, 49, 2412. (k) Ihara, M.; Tsuruta, M.; Fukumoto, K.; Kametani, T. J. Chem. Soc., Chem. Commun. 1985, 1159. (l) Comins, D. L.; Morgan, L. A. Tetrahedron Lett. 1991, 32, 5919. (m) Pearson, W. H.; Walavalkar, R. Tetrahedron Lett. 1994, 50, 12293. (n) Reference 7h.
28. Syntheses of (±)-tylophorine: (a) Govindachari, T. R.; Laksmikantham, M. V.; Rajadurai, S. Tetrahedron 1961, 14, 284-287. (b) Herbert, R. B.; Moody, C. J. J. Chem. Soc. D 1970, 2, 121. (c) Chauncy, B.; Gellert, E. Aust. J. Chem. 1970, 23, 2503. (d) Liepa, A. J.; Summons, R. E. J. Chem. Soc., Chem. Commun. 1977, 826. (e) Weinreb, S. M.; Khatri, N. A.; Shringarpure, J. J. Am. Chem. Soc. 1979, 101, 5073. (f) Mangla, V. K.; Bhakuni, D. S. Tetrahedron 1980, 36, 2489. (g) Khatri, N. A.; Schmitthenner, H. F.; Shringarpure, J.; Weinreb, S. M. J. Am. Chem. Soc. 1981, 103, 6387. (h) Cragg, J. E.; Herbert, R. B.; Jackson, F. B.; Moody, C. J.; Nicholson, I. T. J. Chem. Soc., Perkin Trans. 1 1982, 2477. (i) Iida, H.; Tanaka, M.; Kibayashi, C. J. Chem. Soc., Chem. Commun. 1983, 271. (j) Iida, H.; Watanabe, Y.; Tanaka, M.; Kibayashi, C. J. Org. Chem. 1984, 49, 2412. (k) Ihara, M.; Tsuruta, M.; Fukumoto, K.; Kametani, T. J. Chem. Soc., Chem. Commun. 1985, 1159. (l) Comins, D. L.; Morgan, L. A. Tetrahedron Lett. 1991, 32, 5919. (m) Pearson, W. H.; Walavalkar, R. Tetrahedron Lett. 1994, 50, 12293. (n) Reference 7h.
29. Syntheses of (±)-tylophorine: (a) Govindachari, T. R.; Laksmikantham, M. V.; Rajadurai, S. Tetrahedron 1961, 14, 284-287. (b) Herbert, R. B.; Moody, C. J. J. Chem. Soc. D 1970, 2, 121. (c) Chauncy, B.; Gellert, E. Aust. J. Chem. 1970, 23, 2503. (d) Liepa, A. J.; Summons, R. E. J. Chem. Soc., Chem. Commun. 1977, 826. (e) Weinreb, S. M.; Khatri, N. A.; Shringarpure, J. J. Am. Chem. Soc. 1979, 101, 5073. (f) Mangla, V. K.; Bhakuni, D. S. Tetrahedron 1980, 36, 2489. (g) Khatri, N. A.; Schmitthenner, H. F.; Shringarpure, J.; Weinreb, S. M. J. Am. Chem. Soc. 1981, 103, 6387. (h) Cragg, J. E.; Herbert, R. B.; Jackson, F. B.; Moody, C. J.; Nicholson, I. T. J. Chem. Soc., Perkin Trans. 1 1982, 2477. (i) Iida, H.; Tanaka, M.; Kibayashi, C. J. Chem. Soc., Chem. Commun. 1983, 271. (j) Iida, H.; Watanabe, Y.; Tanaka, M.; Kibayashi, C. J. Org. Chem. 1984, 49, 2412. (k) Ihara, M.; Tsuruta, M.; Fukumoto, K.; Kametani, T. J. Chem. Soc., Chem. Commun. 1985, 1159. (l) Comins, D. L.; Morgan, L. A. Tetrahedron Lett. 1991, 32, 5919. (m) Pearson, W. H.; Walavalkar, R. Tetrahedron Lett. 1994, 50, 12293. (n) Reference 7h.
30. Syntheses of (±)-tylophorine: (a) Govindachari, T. R.; Laksmikantham, M. V.; Rajadurai, S. Tetrahedron 1961, 14, 284-287. (b) Herbert, R. B.; Moody, C. J. J. Chem. Soc. D 1970, 2, 121. (c) Chauncy, B.; Gellert, E. Aust. J. Chem. 1970, 23, 2503. (d) Liepa, A. J.; Summons, R. E. J. Chem. Soc., Chem. Commun. 1977, 826. (e) Weinreb, S. M.; Khatri, N. A.; Shringarpure, J. J. Am. Chem. Soc. 1979, 101, 5073. (f) Mangla, V. K.; Bhakuni, D. S. Tetrahedron 1980, 36, 2489. (g) Khatri, N. A.; Schmitthenner, H. F.; Shringarpure, J.; Weinreb, S. M. J. Am. Chem. Soc. 1981, 103, 6387. (h) Cragg, J. E.; Herbert, R. B.; Jackson, F. B.; Moody, C. J.; Nicholson, I. T. J. Chem. Soc., Perkin Trans. 1 1982, 2477. (i) Iida, H.; Tanaka, M.; Kibayashi, C. J. Chem. Soc., Chem. Commun. 1983, 271. (j) Iida, H.; Watanabe, Y.; Tanaka, M.; Kibayashi, C. J. Org. Chem. 1984, 49, 2412. (k) Ihara, M.; Tsuruta, M.; Fukumoto, K.; Kametani, T. J. Chem. Soc., Chem. Commun. 1985, 1159. (l) Comins, D. L.; Morgan, L. A. Tetrahedron Lett. 1991, 32, 5919. (m) Pearson, W. H.; Walavalkar, R. Tetrahedron Lett. 1994, 50, 12293. (n) Reference 7h.
31. Syntheses of (±)-tylophorine: (a) Govindachari, T. R.; Laksmikantham, M. V.; Rajadurai, S. Tetrahedron 1961, 14, 284-287. (b) Herbert, R. B.; Moody, C. J. J. Chem. Soc. D 1970, 2, 121. (c) Chauncy, B.; Gellert, E. Aust. J. Chem. 1970, 23, 2503. (d) Liepa, A. J.; Summons, R. E. J. Chem. Soc., Chem. Commun. 1977, 826. (e) Weinreb, S. M.; Khatri, N. A.; Shringarpure, J. J. Am. Chem. Soc. 1979, 101, 5073. (f) Mangla, V. K.; Bhakuni, D. S. Tetrahedron 1980, 36, 2489. (g) Khatri, N. A.; Schmitthenner, H. F.; Shringarpure, J.; Weinreb, S. M. J. Am. Chem. Soc. 1981, 103, 6387. (h) Cragg, J. E.; Herbert, R. B.; Jackson, F. B.; Moody, C. J.; Nicholson, I. T. J. Chem. Soc., Perkin Trans. 1 1982, 2477. (i) Iida, H.; Tanaka, M.; Kibayashi, C. J. Chem. Soc., Chem. Commun. 1983, 271. (j) Iida, H.; Watanabe, Y.; Tanaka, M.; Kibayashi, C. J. Org. Chem. 1984, 49, 2412. (k) Ihara, M.; Tsuruta, M.; Fukumoto, K.; Kametani, T. J. Chem. Soc., Chem. Commun. 1985, 1159. (l) Comins, D. L.; Morgan, L. A. Tetrahedron Lett. 1991, 32, 5919. (m) Pearson, W. H.; Walavalkar, R. Tetrahedron Lett. 1994, 50, 12293. (n) Reference 7h.
32. Syntheses of (±)-tylophorine: (a) Govindachari, T. R.; Laksmikantham, M. V.; Rajadurai, S. Tetrahedron 1961, 14, 284-287. (b) Herbert, R. B.; Moody, C. J. J. Chem. Soc. D 1970, 2, 121. (c) Chauncy, B.; Gellert, E. Aust. J. Chem. 1970, 23, 2503. (d) Liepa, A. J.; Summons, R. E. J. Chem. Soc., Chem. Commun. 1977, 826. (e) Weinreb, S. M.; Khatri, N. A.; Shringarpure, J. J. Am. Chem. Soc. 1979, 101, 5073. (f) Mangla, V. K.; Bhakuni, D. S. Tetrahedron 1980, 36, 2489. (g) Khatri, N. A.; Schmitthenner, H. F.; Shringarpure, J.; Weinreb, S. M. J. Am. Chem. Soc. 1981, 103, 6387. (h) Cragg, J. E.; Herbert, R. B.; Jackson, F. B.; Moody, C. J.; Nicholson, I. T. J. Chem. Soc., Perkin Trans. 1 1982, 2477. (i) Iida, H.; Tanaka, M.; Kibayashi, C. J. Chem. Soc., Chem. Commun. 1983, 271. (j) Iida, H.; Watanabe, Y.; Tanaka, M.; Kibayashi, C. J. Org. Chem. 1984, 49, 2412. (k) Ihara, M.; Tsuruta, M.; Fukumoto, K.; Kametani, T. J. Chem. Soc., Chem. Commun. 1985, 1159. (l) Comins, D. L.; Morgan, L. A. Tetrahedron Lett. 1991, 32, 5919. (m) Pearson, W. H.; Walavalkar, R. Tetrahedron Lett. 1994, 50, 12293. (n) Reference 7h.
33. Syntheses of (±)-tylophorine: (a) Govindachari, T. R.; Laksmikantham, M. V.; Rajadurai, S. Tetrahedron 1961, 14, 284-287. (b) Herbert, R. B.; Moody, C. J. J. Chem. Soc. D 1970, 2, 121. (c) Chauncy, B.; Gellert, E. Aust. J. Chem. 1970, 23, 2503. (d) Liepa, A. J.; Summons, R. E. J. Chem. Soc., Chem. Commun. 1977, 826. (e) Weinreb, S. M.; Khatri, N. A.; Shringarpure, J. J. Am. Chem. Soc. 1979, 101, 5073. (f) Mangla, V. K.; Bhakuni, D. S. Tetrahedron 1980, 36, 2489. (g) Khatri, N. A.; Schmitthenner, H. F.; Shringarpure, J.; Weinreb, S. M. J. Am. Chem. Soc. 1981, 103, 6387. (h) Cragg, J. E.; Herbert, R. B.; Jackson, F. B.; Moody, C. J.; Nicholson, I. T. J. Chem. Soc., Perkin Trans. 1 1982, 2477. (i) Iida, H.; Tanaka, M.; Kibayashi, C. J. Chem. Soc., Chem. Commun. 1983, 271. (j) Iida, H.; Watanabe, Y.; Tanaka, M.; Kibayashi, C. J. Org. Chem. 1984, 49, 2412. (k) Ihara, M.; Tsuruta, M.; Fukumoto, K.; Kametani, T. J. Chem. Soc., Chem. Commun. 1985, 1159. (l) Comins, D. L.; Morgan, L. A. Tetrahedron Lett. 1991, 32, 5919. (m) Pearson, W. H.; Walavalkar, R. Tetrahedron Lett. 1994, 50, 12293. (n) Reference 7h.
34. Ihara, M.; Takino, Y.; Tomotake, M.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1 1990, 2287.
35. (a) Comins, D. L.; Joseph, S. P. In Advances in Nitrogen Heterocycles; Moody, C. J., Ed.; JAI Press, Inc.: Greenwich, CT, 1996; Vol. 2, pp 251-294.
36. (b) Comins, D. L.; Zhang, Y. J. Am. Chem. Soc. 1996, 118, 12248 and references cited therein.
37. (a) Comins, D. L.; Joseph, S. P.; Goehring, R. R. J. Am. Chem. Soc. 1994, 116, 4719.
38. (b) Comins, D. L.; Guerra-Weltzien, L. Tetrahedron Lett. 1996, 37, 3807.
39. (a) Comins, D. L.; Salvador, J. M. Tetrahedron Lett. 1993, 34, 801.
40. (b) Comins, D. L.; Salvador, J. M. J. Org. Chem. 1993, 58, 4656.
41. Comins, D. L.; Hong, H. J. Am. Chem. Soc. 1991, 113, 6672.
42. Comins, D. L.; Zeller, E. Tetrahedron Lett. 1991, 32, 5889 and references cited therein.
43. (a) Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1992, 33, 6299.
44. (b) Comins, D. L.; Dehghani, A.; Foti, C. J.; Joseph, S. P. Org. Synth. 1996, 74, 77.