Synthesis of monoterpene piperidines from the iridoid glucoside antirrhinoside

Journal of Natural Products

Volumn 60, Issue 10, 1997, Pages 1012-1016

  Franzyk, Henrik ^a   Frederiksen, Signe M ^a   Jensen, Søren Rosendal ^a  

^a TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

IRIDOID; PIPERIDINE DERIVATIVE; TERPENE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0030774050     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np9702648     Document Type: Article

References (33)

1. Cordell, G. A. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1977, Vol. 16, Chapter 8, pp 470-510.
2. Hammouda, Y.; Le Men, J. Bull. Soc. Chim. France 1963, 2802-2803.
3. Hammouda, Y.; Khalafallah, N. J. Pharm. Sci. 1971, 60, 1142-1145.
4. Hammouda, Y.; Amer, M. S. J. Pharm. Sci. 1966, 55, 1452-1454.
5. Hammouda, Y.; Rashid, A.-K.; Amer, M. S. J. Pharm. Pharmacol. 1964, 16, 833-834.
6. Chi, Y.-M.; Yan, W.-M.; Li, J.-S. Phytochemistry 1990, 29, 2376-2378.
7. Chi, Y.-M.; Yan, W.-M.; Chen, D.-C.; Hiroshi, N.; Yoichi, I.; Ushio, S. Phytochemistry 1992, 31, 2930-2932.
8. Chi, Y.-M.; Hashimoto, F.; Yan, W.-M.; Nohara, T. Phytochemistry 1995, 39, 1485-1487.
9. Chi, Y.-M.; Hashimoto, F.; Yan, W.-M.; Nohara, T. Phytochemistry 1995, 40, 353-354.
10. Kametani, T.; Susuki, Y.; Ban, C.; Honda, T. Heterocycles 1987, 26, 1491-1493.
11. Miyashita, M.; Tanaka, D.; Shiratani, T.; Irie, H. Chem. Pharm. Bull. 1992, 40, 1614-1615.
12. Oppolzer, W.; Jacobsen, E. J. Tetrahedron Lett. 1986, 27, 1141-1144.
13. Cossy, J.; Belotti, D.; Leblanc, C. J. Org. Chem. 1993, 58, 2351-2354.
14. Tsunoda, T.; Ozaki, F.; Shirakata, N.; Tamaoka, Y.; Yamamoto, H.; Itô, S. Tetrahedron Lett. 1996, 37, 2463-2466.
15. Holick, W.; Jenny, E. F.; Heusler, K. Tetrahedron Lett. 1973, 3421-3424.
16. Trede, H.-J.; Jenny, E. F.; Heusler, K. Tetrahedron Lett. 1973, 3425-3428.
17. Allan, R. D.; Fong, J. Aust. J. Chem. 1983, 36, 1221-1226.
18. Larsen, S. D.; Grieco, P. A.; Fobare, W. F. J. Am. Chem. Soc. 1986, 108, 3512-3513.
19. Ogata, M.; Matsumoto, H.; Shimizu, S.; Kida, S.; Nakai, H.; Motokawa, K.; Miwa, H.; Matsuura, S.; Yoshida, T. Eur. J. Med. Chem. 1991, 26, 889-906.
20. Frederiksen, S. M.; Stermitz, F. J. Nat. Prod. 1996, 59, 41-46.
21. Damtoft, S.; Jensen, S. R.; Schacht, M. Phytochemistry 1995, 39, 549-551.
22. McCaig, A. E.; Chomier, B.; Wightman, R. H. J. Carbohydr. Chem. 1994, 13, 397-407.
23. Procopiou, P. A.; Cherry, P. C.; Deal, M. J.; Lamont, R. B. J. Chem. Soc., Perkin Trans. 1 1994, 1773-1777.
24. Scarpati, M. L.; Guiso, M.; Esposito, P. Gazz. Chim. 1968, 98, 177-190.
25. Kitamura, M.; Isobe, M.; Ichikawa, Y.; Goto, T. J. Am. Chem. Soc. 1984, 106, 3252-3257.
26. Nakata, T.; Fukui, M.; Oishi, T. Tetrahedron Lett. 1988, 29, 2219-2222.
27. Shin, J.; Seo, Y. J. Nat. Prod. 1995, 58, 948-953.
28. Bianeo, A.; Guiso, M.; Iavarone, C.; Marini-Bettolo, R.; Trogolo, C. Tetrahedron 1979, 35, 1121-1123.
29. Baxter, E. W.; Reitz, A. B. J. Org. Chem. 1994, 59, 3175-3185.
30. Johnson, C. R.; Golebiowski, A.; Braun, M. P.; Sundram, H. Tetrahedron Lett. 1994, 35, 1833-1834.
31. Furneaux, R. H.; Gainsford, G. J.; Lynch, G. P.; Yorke, S. C. Tetrahedron 1993, 49, 9605-9612.
32. Weinges, K.; Ziegler, H. J.; Schick, H. Liebigs Ann. Chem. 1992, 1213-1216.
33. Chini, M.; Crotti, P.; Gardelli, C.; Macchia, F. J. Org. Chem. 1994, 59, 4131-4137.