Himeradine A, a novel C27N3-type alkaloid from Lycopodium chinense

Journal of Organic Chemistry

Volumn 68, Issue 11, 2003, Pages 4563-4566

  Morita, Hiroshi ^a   Hirasawa, Yusuke ^a   Kobayashi, Jun'ichi ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOIDS;

MOLECULAR STRUCTURE; NITROGEN COMPOUNDS; SPECTROSCOPY; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ORGANIC COMPOUNDS;

ALKALOID; HIMERADINE A; LYCOPODIUM CHINENSE EXTRACT; PLANT EXTRACT; QUINOLIZIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; LYCOPODIUM CHINENSE; MOSS; SPECTROSCOPY; STEREOCHEMISTRY;

EID: 0038779275     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034294t     Document Type: Article

References (27)

1. For reviews of the Lycopodium alkaloids, see: (a) Ayer, W. A.; Trifonov, L. S. In The Alkaloids; Cordell, G. A.; Brossi, A., Ed.; Academic Press: New York, 1994; Vol. 45, p 233. (b) Ayer, W. A. Nat. Prod. Rep. 1991, 8, 455. (c) D. B. MacLean. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1985; Vol. 26, p 241. (d) D. B. MacLean. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1973; Vol. 14, p 348. (e) D. B. MacLean. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1968; Vol. 10, p 305.
2. For reviews of the Lycopodium alkaloids, see: (a) Ayer, W. A.; Trifonov, L. S. In The Alkaloids; Cordell, G. A.; Brossi, A., Ed.; Academic Press: New York, 1994; Vol. 45, p 233. (b) Ayer, W. A. Nat. Prod. Rep. 1991, 8, 455. (c) D. B. MacLean. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1985; Vol. 26, p 241. (d) D. B. MacLean. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1973; Vol. 14, p 348. (e) D. B. MacLean. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1968; Vol. 10, p 305.
3. For reviews of the Lycopodium alkaloids, see: (a) Ayer, W. A.; Trifonov, L. S. In The Alkaloids; Cordell, G. A.; Brossi, A., Ed.; Academic Press: New York, 1994; Vol. 45, p 233. (b) Ayer, W. A. Nat. Prod. Rep. 1991, 8, 455. (c) D. B. MacLean. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1985; Vol. 26, p 241. (d) D. B. MacLean. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1973; Vol. 14, p 348. (e) D. B. MacLean. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1968; Vol. 10, p 305.
4. For reviews of the Lycopodium alkaloids, see: (a) Ayer, W. A.; Trifonov, L. S. In The Alkaloids; Cordell, G. A.; Brossi, A., Ed.; Academic Press: New York, 1994; Vol. 45, p 233. (b) Ayer, W. A. Nat. Prod. Rep. 1991, 8, 455. (c) D. B. MacLean. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1985; Vol. 26, p 241. (d) D. B. MacLean. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1973; Vol. 14, p 348. (e) D. B. MacLean. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1968; Vol. 10, p 305.
5. For reviews of the Lycopodium alkaloids, see: (a) Ayer, W. A.; Trifonov, L. S. In The Alkaloids; Cordell, G. A.; Brossi, A., Ed.; Academic Press: New York, 1994; Vol. 45, p 233. (b) Ayer, W. A. Nat. Prod. Rep. 1991, 8, 455. (c) D. B. MacLean. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1985; Vol. 26, p 241. (d) D. B. MacLean. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1973; Vol. 14, p 348. (e) D. B. MacLean. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1968; Vol. 10, p 305.
6. (a) Hemscheidt, T.; Spenser, I. D. J. Am. Chem. Soc. 1996, 118, 1799-1800.
7. (b) Hemscheidt, T.; Spenser, I. D. J. Am. Chem. Soc. 1993, 115, 3020-3021.
8. Liu, J. S.; Zhu, Y. L.; Yu, C. M.; Zhou, Y. Z.; Han, Y. Y.; Wu, F. W.; Qi, B. F. Can. J. Chem. 1986, 64, 837-839.
9. (a) Sha, C.-K.; Lee, F.-K.; Chang, C.-J. J. Am. Chem. Soc. 1999, 121, 9875-9876.
10. (b) Williams, J. P.; St. Laurent, D. R.; Friedrich, D.; Pinard, E.; Roden, B. A.; Paquette, L. A. J. Am. Chem. Soc. 1994, 116, 4689-4696.
11. (c) Hirst, G. C.; Johnson, T. O.; Overman, L. E. J. Am. Chem. Soc. 1993, 115, 2992-2993, and references therein.
12. Morita, H.; Arisaka, M.; Yoshida, N.; Kobayashi, J. J. Org. Chem. 2000, 65, 6241-6245.
13. Kobayashi, J.; Hirasawa, Y.; Yoshida, N.; Morita, H. Tetrahedron Lett. 2000, 41, 9069-9073.
14. Kobayashi, J.; Hirasawa, Y.; Yoshida, N.; Morita, H. J. Org. Chem. 2001, 66, 5901-5904.
15. Morita, H.; Hirasawa, Y.; Yoshida, N.; Kobayashi, J. Tetrahedron Lett. 2001, 42, 4199-4201.
16. Hirasawa, Y.; Morita, H.; Kobayashi, J. Tetrahedron 2002, 58, 5483-5488.
17. Ayer, W. A.; Browne, L. M.; Nakahara, Y.; Tori, M. Can. J. Chem. 1979, 57, 1105-1107; Tori, M.; Shimoji, T.; Takaoka, S.; Nakashima, K.; Sono, M.; Ayer, W. A. Tetrahedron Lett. 1999, 40, 323-324; Tori, M.; Shimoji, T.; Shimura, E.; Takaoka, S.; Nakashima, K.; Sono, M.; Ayer, W. A. Phytochemistry 2000, 53, 503-509.
18. Ayer, W. A.; Browne, L. M.; Nakahara, Y.; Tori, M. Can. J. Chem. 1979, 57, 1105-1107; Tori, M.; Shimoji, T.; Takaoka, S.; Nakashima, K.; Sono, M.; Ayer, W. A. Tetrahedron Lett. 1999, 40, 323-324; Tori, M.; Shimoji, T.; Shimura, E.; Takaoka, S.; Nakashima, K.; Sono, M.; Ayer, W. A. Phytochemistry 2000, 53, 503-509.
19. Ayer, W. A.; Browne, L. M.; Nakahara, Y.; Tori, M. Can. J. Chem. 1979, 57, 1105-1107; Tori, M.; Shimoji, T.; Takaoka, S.; Nakashima, K.; Sono, M.; Ayer, W. A. Tetrahedron Lett. 1999, 40, 323-324; Tori, M.; Shimoji, T.; Shimura, E.; Takaoka, S.; Nakashima, K.; Sono, M.; Ayer, W. A. Phytochemistry 2000, 53, 503-509.
20. Ayer, W. A.; Iverach, G. G. Can. J. Chem. 1964, 42, 2514-2522.
21. The iminium carbon (C-13) observed at δ 196.7 for TFA salt of 1 was shifted to δ 170.1 for free base. Some examples; Kobayashi, J.; Ueno, S.; Morita, H. J. Org. Chem. 2002, 67, 6546-6549; Kobayashi, J.; Inaba, Y.; Shiro, M.; Yoshida, N.; Morita, H. J. Am. Chem. Soc. 2001, 123, 11402-11408; Uemura, D.; Chou, T.; Haino, T.; Nagatsu, A.; Fukuzawa, S.; Zheng, S.-z.; Chem, H.-s. J. Am. Chem. Soc. 1995, 117, 1155-1156.
22. The iminium carbon (C-13) observed at δ 196.7 for TFA salt of 1 was shifted to δ 170.1 for free base. Some examples; Kobayashi, J.; Ueno, S.; Morita, H. J. Org. Chem. 2002, 67, 6546-6549; Kobayashi, J.; Inaba, Y.; Shiro, M.; Yoshida, N.; Morita, H. J. Am. Chem. Soc. 2001, 123, 11402-11408; Uemura, D.; Chou, T.; Haino, T.; Nagatsu, A.; Fukuzawa, S.; Zheng, S.-z.; Chem, H.-s. J. Am. Chem. Soc. 1995, 117, 1155-1156.
23. The iminium carbon (C-13) observed at δ 196.7 for TFA salt of 1 was shifted to δ 170.1 for free base. Some examples; Kobayashi, J.; Ueno, S.; Morita, H. J. Org. Chem. 2002, 67, 6546-6549; Kobayashi, J.; Inaba, Y.; Shiro, M.; Yoshida, N.; Morita, H. J. Am. Chem. Soc. 2001, 123, 11402-11408; Uemura, D.; Chou, T.; Haino, T.; Nagatsu, A.; Fukuzawa, S.; Zheng, S.-z.; Chem, H.-s. J. Am. Chem. Soc. 1995, 117, 1155-1156.
24. Gerard, R. V.; Maclean, D. B.; Fagianni, R.; Lock, C. J. Can. J. Chem. 1986, 64, 943-949.
25. Conformational search and molecular mechanics calculations were conducted by Macromodel program: Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440-467.
26. Halgren, T. J. Am. Chem. Soc. 1990, 112, 4710-4723.
27. Ayer, W. A.; Browne, L. M.; Nakahara, Y.; Tori, M. Can. J. Chem. 1979, 57, 1105-1107.