Synthesis of C5-substituted AE-bicyclic analogues of lycoctonine, inuline and methyllycaconitine

Tetrahedron Letters

Volumn 39, Issue 8, 1998, Pages 889-892

  Grangier, Géraldine ^a   Trigg, William J ^a   Lewis, Terence ^b   Rowan, Michael G ^a   Potter, Barry V L ^a   Blagbrough, Ian S ^a  

^a University of Bath   (United Kingdom)

^b JEALOTT S HILL RESEARCH STATION   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; ALKALOID; INULIN; KETONE; LYCOCTONINE; METHYLLYCACONITINE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DIASTEREOISOMER; DRUG SYNTHESIS; NONHUMAN;

EID: 0032546075     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10648-7     Document Type: Article

References (32)

1. 1. Manske, R. H. Can. J. Research 1938, 16B, 57-60.
2. 2. Goodson, J. A. J. Chem. Soc. 1943, 139-141.
3. 3. Keeler, R. F. Lloydia 1975, 38, 56-61.
4. 4. Manners, G. D.; Panter, K. P.; Pelletier, S. W. J. Nat. Prod. 1995, 58, 863-869.
5. 5. Nambi Aiyar, V.; Benn, M. H.; Hanna, T.; Jacyno, J.; Roth, S. H.; Wilkens, J. L. Experientia 1979, 35, 1367-1368.
6. 6. Jennings, K. R.; Brown, D. G.; Wright, D. P. Experientia 1986, 42, 611-613.
7. 7. Plinius, G. Naturalis Historia AD77, Book 23, Chapter 13.
8. 8. Benn, M. H.; Jacyno, J. M. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; John Wiley and Sons: New York, 1983, 1, pp. 153-210.
9. 9. Wonnacott, S.; Albuquerque, E. X.; Bertrand D. In Methods in Neurosciences; Conn, M., Ed.; Academic Press: New York, 1993, 12, pp. 263-275.
10. 10. Jennings, K. R.; Brown, D. G.; Wright, D. P.; Chalmers, A. E. ACS Symposium Series 1987, 356, 316-325.
11. 11. Baillie, L. C.; Bearder, J. R.; Whiting, D. A. J. Chem. Soc., Chem. Commun. 1994, 2487-2488.
12. 12. Baillie, L. C.; Bearder, J. R.; Sherringham, J. A.; Whiting, D. A. J. Chem. Soc., Perkin Trans. 1 1997, 2687-2688.
13. 13. Kraus, G. A.; Andersh, B.; Su, Q.; Shi, J. Tetrahedron Lett. 1993, 34, 1741-1744.
14. 14. van Beek, G.; van der Baan, J. L.; Klumpp, G. W.; Bickelhaupt, F. Tetrahedron 1986, 42, 5111-5122.
15. 15. van der Baan, J. L.; Barnick, J. W. F. K.; van Beek, G.; Bickelhaupt, F.; Spek, A. L. Tetrahedron 1992, 48, 2773-2784.
16. 16. Labriola, R.; Ourisson, G. Tetrahedron 1973, 29, 2105-2114.
17. 17. Montalbetti, C.; Savignac, M.; Bonnefis, F.; Genêt, J. P. Tetrahedron Lett. 1995, 36, 5891-5894.
18. 18. Coates, P. A.; Blagbrough, I. S.; Rowan, M. G.; Potter, B. V. L.; Pearson, D. P. J.; Lewis, T. Tetrahedron Lett. 1994, 35, 8709-8712.
19. 19. Shimizu, B.; Ogiso, A.; Iwai, I. Chem. Pharm. Bull. 1963, 11, 333-336.
20. 20. Ihara, M.; Suzuki, M.; Fukumoto, K.; Kametani, T.; Kabuto, C. J. Am. Chem. Soc. 1988, 110, 1963-1964.
21. 21. Marshall, J. A.; Karas, L. J.; Royce Jr., R. D. J. Org. Chem. 1979, 44, 2994-2999.
22. 22. Buhler, J. D. J. Org. Chem. 1973, 38, 904-906.
23. 23. Milas, N. A.; Macdonald, N. S.; Black, D. M. J. Am. Chem. Soc. 1948, 70, 1829-1834.
24. 24. Attenburrow, J.; Cameron, A. F. B.; Chapman, J. H.; Evans, R. M.; Hems, B. A.; Jansen, A. B. A.; Walker, T. J. Chem. Soc. 1952, 1094-1111.
25. 25. Olson, G. L.; Cheung, H.-C.; Morgan, K. D.; Borer, R.; Saucy, G. Helv. Chim. Acta 1976, 59, 567-585.
26. 26. Shimizu, B.; Ogiso, A.; Iwai, I. Chem. Pharm. Bull. 1963, 11, 760-769.
27. 27. Hollinshead, D. M.; Howell, S. C.; Ley, S. V.; Mahon, M.; Ratcliffe, N. M.; Worthington, P. A. J. Chem. Soc., Perkin Trans. 1 1983, 1579-1589.
28. 28. Weyerstahl, P.; Buchmann, B.; Marschall-Weyerstahl, H. Liebigs Ann. Chem. 1988, 507-523.
29. 29. Weyerstahl, P.; Meisel T. Liebigs Ann. Chem. 1994, 415-427.
30. 30. Gorthey, L. A.; Vairamani, M.; Djerassi, C. J. Org. Chem. 1985, 50, 4173-4187.
31. 31. Bowen, J. P.; Allinger N. L. J. Org. Chem. 1987, 52, 1830-1834.
32. 32. Blagbrough, I. S.; Coates, P. A.; Hardick, D. J.; Lewis, T.; Rowan, M. G.; Wonnacott, S.; Potter, B. V. L. Tetrahedron Lett. 1994, 35, 8705-8708.