Daphnezomines A and B, novel alkaloids with an aza-adamantane core from Daphniphyllum humile

Journal of Organic Chemistry

Volumn 64, Issue 19, 1999, Pages 7208-7212

  Morita, Hiroshi ^a   Yoshida, Naotoshi ^a   Kobayashi, Jun'ichi ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ADAMANTANE DERIVATIVE; ALKALOID; DAPHNEZOMINE A; DAPHNEZOMINE B; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; EXTRACTION; MOLECULAR MODEL; NONHUMAN; PLANT; PLANT LEAF; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0033578933     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990882o     Document Type: Article

References (37)

1. For reviews of the Daphniphyllum alkaloids, see: (a) Yamamura, S.; Hirata, Y. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1975; Vol. 15, p 41.
2. (b) Yamamura, S. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1986; Vol. 29, p 265.
3. (a) Hao, X.; Zhou, J.; Node, M.; Fuji, K. Yunnan Zhiwu Yanjiu 1993, 15, 205-207.
4. (b) Arbain, D.; Byrne, L. T.; Cannon, J. R.; Patrick, V. A.; White, A. H. Aust. J. Chem. 1990, 43, 185-190.
5. (c) Yamamura, S.; Lamberton, J. A.; Niwa, M., Endo, K., Hirata, Y. Chem. Lett. 1980, 393-396.
6. Yamamura, S.; Toda, M.; Hirata, Y. Bull. Chem. Soc. Jpn. 1976, 49, 839.
7. (e) Yamamura, S.; Lamberton, J. A.; Irikawa, H.; Okumura, Y.; Hirata, Y. Chem. Lett. 1976, 923-926.
8. (f) Yamamura, S.; Irikawa, H.; Okumura, Y.; Hirata, Y. Bull. Chem. Soc. Jpn. 1975, 48, 2120-2123.
9. (g) Yamamura, S.; Hirata, Y. Tetrahedron Lett. 1974, 42, 3673-3676.
10. (h) Yamamura, S.; Sasaki, K.; Toka, M.; Hirata, Y. Tetrahedron Lett. 1974, 2023-2026 and references therein.
11. (a) Heathcock, C. H. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 14323-14327.
12. (b) Heathcock, C. H.; Joe, D. J. Org. Chem. 1995, 60, 1131-1142.
13. Heathcock, C. H.; Kath, J. C.; Ruggeri, R. B. J. Org. Chem. 1985, 60, 1120-1130.
14. Heathcock, C. H. Angew. Chem. 1992, 104, 675-691; Angew. Chem., Int. Ed. Engl. 1992, 31, 665-681 and references therein.
15. Heathcock, C. H. Angew. Chem. 1992, 104, 675-691; Angew. Chem., Int. Ed. Engl. 1992, 31, 665-681 and references therein.
16. (a) In the previous study, yuzurimine was isolated as a major alkaloid together with secodaphniphylline, daphniteijsmine, deoxyyuzurimine, and isodaphnilactone-B: Yamamura, S.; Terada, Y. Chem. Lett. 1976, 1381-1382.
17. (b) A disease with jaundice, colic, and photophobia as main symptoms that had broken out among grazing cattle in Hokkaido was demonstrated to be a plant poisoning caused by D. humile which contained a toxic substance affecting the liver specifically: Sonoda, M.; Tasaka, M.; Takahashi, K.; Koiwa, M.; Minami, S.; Iwasa, M.; Yashiro, K. J. Jpn. Vet. Med. Assoc. 1978, 31, 140-144.
18. c 85-95 ppm: Lindquist. N.; Fenical, W. Tetrahedron Lett. 1990, 31, 2521-2524.
19. c 85-95 ppm: Lindquist. N.; Fenical, W. Tetrahedron Lett. 1990, 31, 2521-2524.
20. Edwards, M. W.; Bax, A. J. Am. Chem. Soc. 1986, 108, 918-923.
21. (a) Bax, A.; Summers, M. F. J. Am. Chem. Soc. 1986, 108, 2093-2094.
22. (b) Bax, A.; Aszalos, A.; Dinya, Z.; Sudo, K. J. Am. Chem. Soc. 1986, 108, 8056-8063.
23. Lerner, L.; Bax, A. J. Magn. Reson. 1986, 69, 375-380.
24. 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.
25. b-16/H-1) are indicative of the chair-chair form in two azabicyclo[3.3.1]nonane parts (N-1 and C-1-C-8, and N-1, C-1, C-8-C-11, and C-15-C-17): Appleton, R. A.; Egan, S. C.; Evans, J. M.; Graham, S. H.; Dixon, J. R. J. Chem. Soc. C 1968, 1110-1115.
26. -1) for 4, whereas it was not observed for the free base of 2. To examine the spectroscopic anomalies, yuzurimine free base with the similar amino ketal functionality was prepared under the same conditions, but such spectroscopic anomalies were not observed.
27. Flack, H. D. Acta Crystallogr. 1983, A39, 876-881.
28. 1-Aza-adamantanes have explicitly been used as rigid models for studies on heterolytic fragmentation (Grob, C. A.; Bolleter, M.; Kunz, W. Angew. Chem. 1980, 92, 734-735), intramolecular charge-transfer phenomena (Worrell, C.; Verhoeven, J. W.; Speckamp, W. N. Tetrahedron 1974, 30, 3525-3531), and gas-phase basicity: Dekkers, A. W. J. D.; Nibbering, N. M. M.; Speckamp, W. N. Tetrahedron 1972, 28, 1829.
29. 1-Aza-adamantanes have explicitly been used as rigid models for studies on heterolytic fragmentation (Grob, C. A.; Bolleter, M.; Kunz, W. Angew. Chem. 1980, 92, 734-735), intramolecular charge-transfer phenomena (Worrell, C.; Verhoeven, J. W.; Speckamp, W. N. Tetrahedron 1974, 30, 3525-3531), and gas-phase basicity: Dekkers, A. W. J. D.; Nibbering, N. M. M.; Speckamp, W. N. Tetrahedron 1972, 28, 1829.
30. 1-Aza-adamantanes have explicitly been used as rigid models for studies on heterolytic fragmentation (Grob, C. A.; Bolleter, M.; Kunz, W. Angew. Chem. 1980, 92, 734-735), intramolecular charge-transfer phenomena (Worrell, C.; Verhoeven, J. W.; Speckamp, W. N. Tetrahedron 1974, 30, 3525-3531), and gas-phase basicity: Dekkers, A. W. J. D.; Nibbering, N. M. M.; Speckamp, W. N. Tetrahedron 1972, 28, 1829.
31. 18
32. Goto, T.; Kishi, Y.; Takahashi, S.; Hirata, Y. Tetrahedron Lett. 1964, 779-786; Tetrahedron 1965, 21, 2059-2088. Woodward, R. B. Pure Appl. Chem. 1964, 9, 49-74.
33. Goto, T.; Kishi, Y.; Takahashi, S.; Hirata, Y. Tetrahedron Lett. 1964, 779-786; Tetrahedron 1965, 21, 2059-2088. Woodward, R. B. Pure Appl. Chem. 1964, 9, 49-74.
34. Goto, T.; Kishi, Y.; Takahashi, S.; Hirata, Y. Tetrahedron Lett. 1964, 779-786; Tetrahedron 1965, 21, 2059-2088. Woodward, R. B. Pure Appl. Chem. 1964, 9, 49-74.
35. Roll, D. M.; Biskupiak, J. E.; Mayne, C. L.; Ireland, C. M. J. Am. Chem. Soc. 1986, 108, 6680-6682.
36. Monta, Y.; Hesse, M.; Schmid, H.; Banerji, A.; Banerji, J.; Chatterjee, A.; Oberhansli, W. E. Helv. Chim. Acta 1977, 60, 1419-1434.
37. Borschberg, H.-J. Helv. Chim. Acta 1984, 67, 1878-1882.