Enantiospecific synthesis of (+)- and (-)-ferruginine from L-glutamic acid. Synthesis of tropanes via intramolecular iminium ion cyclization

Journal of Organic Chemistry

Volumn 61, Issue 1, 1996, Pages 314-323

  Hernández, Andrés S ^a   Thaler, Adrian ^a   Castells, Josep ^a   Rapoport, Henry ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; FERRUGININE; TROPANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030050041     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9515081     Document Type: Article

References (30)

1. Bick, I. R. C.; Gillard, J. W.; Leow, H.-M. Aust. J. Chem. 1979, 32, 2537.
2. Bick, I. R. C.; Gillard, J. W.; Leow, H.-M. Aust. J. Chem. 1979, 32, 2523.
3. Swanson, K. L.; Albuquerque, E. X. Handbook of Expt. Pharmacology, Vol. 102. Selective Neurotoxicity; Herken, H., Hucho, F. Eds.; Springer-Verlag: Berlin, Heidelberg, 1992; pp 620-621.
4. (a) Sardina, F. J.; Howard, M. H.; Morningstar, M.; Rapoport, H. J. Org. Chem. 1990, 55, 5025.
5. (b) Hernández, A.; Rapoport, H. J. Org. Chem. 1994, 59, 1058.
6. Hernández, A.; Marcos, M.; Rapoport, H. J. Org. Chem. 1995, 60, 2683.
7. Petersen, J. S.; Fels, G.; Rapoport, H. J. Am. Chem. Soc. 1984, 106, 4539 and ref 4a therein.
8. Shiosaki, K.; Fels, G.; Rapoport, H. J. Org. Chem. 1981, 46, 3230 and refs 12-15 therein.
9. Hsung, R. P. Synth. Commun. 1990, 20, 1175.
10. Negishi, E.; Boardman, L. D.; Sawada, H.; Bagheri, V.; Stoll, A. T.; Tour, J. M.; Rand, C. L. J. Am. Chem. Soc. 1988, 110, 5383.
11. Kelly, T. R.; Schmidt, T. E.; Haggerty, J. G. Synthesis 1972, 544.
12. Janout, V.; Regen, S. L. J. Org. Chem. 1982, 47, 3331.
13. (a) Davis, F. A; Vishwakarma, L. C.; Billmers J. M.; Finn, J. J. Org. Chem. 1984, 49, 3241.
14. (b) Vishwakarma, L. C.; Stringer, O. D.; Davis, F. A. Org. Synth. 1988, 66, 203.
15. (c) Davis, F. A.; Chattopadhyay, S.; Towson, J. C.; Lal, S.; Reddy T. J. Org. Chem. 1988, 53, 2087.
16. 1H NMR spectrum.
17. Sardina, F. J.; Howard, M. H.; Koskinen, A. M. P.; Rapoport, H. J. Org. Chem. 1989, 54, 4654.
18. The authors have deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U.K.
19. (a) Barton, D. H. R.; Hervé, Y.; Potier, P.; Thierry, J. Tetrahedron 1988, 44, 5479.
20. (b) Barton, D. H. R.; Bridon, D.; Fernandez-Picot, I; Zard, S. Z. Tetrahedron 1987, 43, 2733.
21. Barton, D. H. R.; Bridon, D; Zard, S. Z. Heterocycles 1987, 25, 449.
22. (a) Raederstorff, D., Shu, A. Y. L.; Thompson, J. E.; Djerassi, C. J. Org. Chem. 1987, 52, 2337.
23. (b) Zoretic, P. A.; Chambers, R. J.; Marbury, G. D ; Riebiro, A. A. J. Org. Chem. 1985, 50, 2981.
24. Howard, M. H.; Sardina, F. J.; Rapoport, H. J. Org. Chem. 1990, 55 , 2829.
25. Davies, H. M. L.; Saikali, E.; Young, W. B. J. Org. Chem. 1991, 56, 5696.
26. Campbell, H. F.; Edwards, O. E.; Kolt, R. Can. J. Chem. 1977, 55, 1372.
27. Lukes, R.; Dolezal, S.; Capek, K. Collect. Czech. Chem. Commun. 1962, 27, 2408.
28. Magnusson, G. Tetrahedron 1978, 34, 1385.
29. Machleidt, H. v.; Cohnen, E.; Tschesche, R. Liebigs Ann. Chem. 1962, 655, 70.
30. Solladié, G; Maestro, M. C.; Rubio, A; Pedregal C.; Carreño, M. C.; Ruano, J. L. G. J. Org. Chem. 1991, 56, 2317.