Calyciphylline D, a novel alkaloid with an unprecedented fused-pentacyclic skeleton from daphniphyllum calycinum

Organic Letters

Volumn 9, Issue 7, 2007, Pages 1207-1209

  Saito, Shizuka ^a   Kubota, Takaaki ^a   Fukushi, Eri ^a   Kawabata, Jun ^a   Zhang, Huiping ^b   Kobayashi, Jun'ichi ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

^b FUDAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; CALYCIPHYLLINE D; FUSED HETEROCYCLIC RINGS; HETEROCYCLIC COMPOUND; POLYCYCLIC HYDROCARBON; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ISOLATION AND PURIFICATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PLANT LEAF; SAXIFRAGACEAE; STEREOISOMERISM;

ALKALOIDS; AZA COMPOUNDS; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PLANT LEAVES; POLYCYCLIC COMPOUNDS; SAXIFRAGACEAE; STEREOISOMERISM;

EID: 34147190995     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0631455     Document Type: Article

References (36)

1. For a review of Daphniphyllum alkaloids, see: Kobayashi, J.; Monta, H. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 2003; Vol. 60, pp 165-205 and references therein.
2. (a) Saito, S.; Kubota, T.; Fukushi, E.; Kawabata, J.; Zhang, H.; Kobayashi, J. Tetrahedron Lett. 2007, 48, 1587-1589.
3. (b) Morita, H.; Ishioka, N.; Takatsu, H.; Iizuka, T.; Kobayashi, J. J. Nat. Prod. 2006, 69, 418-420.
4. (c) Kubota, T.; Matsuno, Y.; Morita, H.; Shinzato, T.; Sekiguchi, M.; Kobayashi, J. Tetrahedron 2006, 62, 4743-4748.
5. (d) Morita, H.; Ishioka, N.; Takatsu, H.; Shinzato, T.; Obara, Y.; Nakahata, N.; Kobayashi, J. Org. Lett. 2005, 7, 459-462.
6. (e) Takatsu, H.; Morita, H.; Shen, Y. C.; Kobayashi, J. Tetrahedron 2004, 60, 6279-6284.
7. (f) Morita, H.; Takatsu, H.; Shen, Y. C.; Kobayashi, J. Tetrahedron Lett. 2004, 45, 901-904.
8. (g) Morita, H.; Kobayashi, J. Org. Lett. 2003, 5, 2895-2898.
9. (h) Kobayashi, J.; Takatsu, H.; Shen, Y. C.; Morita, H. Org. Lett. 2003, 5, 1733-1736.
10. (i) Morita, H.; Takatsu, H.; Kobayashi, J. Tetrahedron 2003, 59, 3575-3579.
11. (a) Bitar, H. E.; Nguyen, V. H.; Gramain, A.; Sévenet, T.; Bodo, B. Tetrahedron Lett. 2004, 45, 515-518.
12. (b) Bitar, H. E.; Nguyen, V. H.; Gramain, A.; Sévent, T.; Bodo, B. J. Nat. Prod. 2004, 67, 1094-1099.
13. Zhang, W.; Guo, Y.-W.; Krohn, K. Chem. - Eur. J. 2006, 12, 5122-5127.
14. Jossang, A.; Bitar, H. E.; Pham, V. C.; Sévenet, T. J. Org. Chem. 2003, 68, 300-304.
15. (a) Di, Y. T.; He, H. P.; Lu, Y.; Yi, P.; Li, L.; Wu, L.; Hao, X. J. J. Nat. Prod. 2006, 69, 1074-1076.
16. (b) Mu, S. Z.; Wang, Y.; He, H. P.; Yang, X. W.; Wang, Y. H.; Di, Y. T.; Lu, Y.; Chang, Y.; Hao, X. J. J. Nat. Prod. 2006, 69, 1065-1069.
17. (c) Li, L.; He, H. P.; Di, Y. T.; Tian, J. M.; Hao, X. J. Helv. Chim. Acta 2006, 89, 1457-1462.
18. (d) Li, L.; He, H. P.; Di, Y. T.; Gao, S.; Hao, X.-J. Tetrahedron Lett. 2006, 47, 6259-6262.
19. (e) Di, Y. T.; He, H. P.; Liu, H. Y.; Du, Z. Z.; Tian, J. M.; Yang, X. W.; Wang, Y. H.; Hao, X. J. Tetrahedron Lett. 2006, 47, 5329-5331.
20. (a) Fan, C. Q.; Yin, S.; Xue, J. J.; Yue, J. M. Tetrahedron, 2007, 63, 115-119.
21. (b) Zhang, H.; Yang, S. P.; Fan, C. Q.; Ding, J.; Yue, J. M. J. Nat. Prod. 2006, 69, 553-557.
22. (c) Yang, S. P.; Zhang, H.; Zhang, C. R.; Cheng, H. D.; Yue, J. M. J. Nat. Prod. 2006, 69, 79-82.
23. (d) Zhan, Z. J.; Zhang, C. R.; Yue, J. M. Tetrahedron 2005, 61, 11038-11045.
24. (e) Chen, X.; Zhan, Z. J.; Yue, J. M. Helv. Chim. Acta 2005, 88, 854-860.
25. (f) Chen, H.; Zhang, Z. J.; Yue, J. M. Chem. Biodivers. 2004, 1, 1513-1518.
26. (g) Zhan, Z. J.; Yang, S. P.; Yue, J. M. J. Org. Chem. 2004, 69, 1726-1729.
27. (h) Yang, S. P.; Yue, J. M. Org. Lett. 2004, 6, 1401-1404.
28. (i) Yang, S. P.; Yue, J. M. J. Org. Chem. 2003, 68, 7961-7966.
29. (a) Wallace, G. A.; Heathcock, C. H. J. Org. Chem. 2001, 66, 450-454.
30. (b) Heathcock, C. H. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 14323-14327.
31. (c) Heathcock, C. H.; Joe, D. J. Org. Chem. 1995, 60, 1131-1142.
32. (d) Heathcock, C. H.; Kath, J. C.; Ruggeri, R. B. J. Org. Chem. 1995, 60, 1120-1130.
33. (e) Heathcock, C. H. Angew. Chem. 1992, 104, 675-691.
34. (f) Heathcock, C. H. Angew. Chem., Int. Ed. Engl. 1992, 31, 665-681 and references cited therein.
35. 3, 456.3478]).
36. Kamijo, N.; Nakano, T.; Terao, S.; Osaki, K. Tetrahedron Lett. 1966, 2889-2892.