95. Asymmetric synthesis of the alkaloids mayfoline and N(1)-Acetyl-N(1)-deoxymayfoline

Helvetica Chimica Acta

Volumn 79, Issue 4, 1996, Pages 1085-1094

  Kuehne, Paul ^a   Linden, Anthony ^a   Hesse, Manfred ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; MAYFOLINE; N1 ACETYL N1 DEOXYMAYFOLINE; POLYAMINE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CIRCULAR DICHROISM; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY ANALYSIS;

EID: 0029973102     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.19960790417     Document Type: Article

References (34)

1. A. Guggisberg, M Hesse, in 'The Alkaloids'. Ed A. Brossi, Academic Press, Inc., New York, 1983, Vol. 22, pp 85-188
2. B Ganem, Acc. Chem Res. 1982, 15, 290.
3. R. P. Robinson, Dissertation, Yale University, 1984.
4. H. Ripperger, Phytochemistry 1980, 19, 162.
5. J. S. McManis, B. Ganem, J. Org Chem. 1980, 45, 2041.
6. H H. Wasserman, R. P. Robinson, H Matsuyama, Tetrahedron Lett. 1980, 21, 3493; H H. Wasserman, H. Matsuyama, J. Am Chem. Soc. 1981, 103, 461; H. H Wasserman, R. P. Robinson, Tetrahedron Lett. 1983, 24, 3669; H. H. Wasserman, G D Berger, Tetrahedron 1983, 39, 2459, H H. Wasserman, Aldrichim. Acta 1987, 20, 63.
7. H H. Wasserman, R. P. Robinson, H Matsuyama, Tetrahedron Lett. 1980, 21, 3493; H H. Wasserman, H. Matsuyama, J. Am Chem. Soc. 1981, 103, 461; H. H Wasserman, R. P. Robinson, Tetrahedron Lett. 1983, 24, 3669; H. H. Wasserman, G D Berger, Tetrahedron 1983, 39, 2459, H H. Wasserman, Aldrichim. Acta 1987, 20, 63.
8. H H. Wasserman, R. P. Robinson, H Matsuyama, Tetrahedron Lett. 1980, 21, 3493; H H. Wasserman, H. Matsuyama, J. Am Chem. Soc. 1981, 103, 461; H. H Wasserman, R. P. Robinson, Tetrahedron Lett. 1983, 24, 3669; H. H. Wasserman, G D Berger, Tetrahedron 1983, 39, 2459, H H. Wasserman, Aldrichim. Acta 1987, 20, 63.
9. H H. Wasserman, R. P. Robinson, H Matsuyama, Tetrahedron Lett. 1980, 21, 3493; H H. Wasserman, H. Matsuyama, J. Am Chem. Soc. 1981, 103, 461; H. H Wasserman, R. P. Robinson, Tetrahedron Lett. 1983, 24, 3669; H. H. Wasserman, G D Berger, Tetrahedron 1983, 39, 2459, H H. Wasserman, Aldrichim. Acta 1987, 20, 63.
10. H H. Wasserman, R. P. Robinson, H Matsuyama, Tetrahedron Lett. 1980, 21, 3493; H H. Wasserman, H. Matsuyama, J. Am Chem. Soc. 1981, 103, 461; H. H Wasserman, R. P. Robinson, Tetrahedron Lett. 1983, 24, 3669; H. H. Wasserman, G D Berger, Tetrahedron 1983, 39, 2459, H H. Wasserman, Aldrichim. Acta 1987, 20, 63.
11. H. Yamamoto, K. Maruoka, J. Am. Chem. Soc. 1981, 103, 6133.
12. T. Kaseda, T. Kikuchi, C. Kibayashi, Tetrahedron Lett. 1989, 30, 4539.
13. H. H. Wasserman, G. D. Berger, Tetrahedron 1983, 39, 2459.
14. K. Ishihara, Y. Kuroki, H. Yamamoto, Synlett 1995, 41.
15. H. Matsuyama, M. Kobayashi, H.H. Wasserman, Heterocycles 1987, 26, 85.
16. G. W. Gribble, P. D. Lord, J. Skotnicki, S. E. Dietz, J. T. Eaton, J. L. Johnson, J. Am. Chem. Soc. 1974, 96, 7812; G. W. Gribble, P. W. Heald, Synthesis 1975, 650; P Marchini, G. Liso, A. Reho, J. Org. Chem. 1975, 40, 3453.
17. G. W. Gribble, P. D. Lord, J. Skotnicki, S. E. Dietz, J. T. Eaton, J. L. Johnson, J. Am. Chem. Soc. 1974, 96, 7812; G. W. Gribble, P. W. Heald, Synthesis 1975, 650; P Marchini, G. Liso, A. Reho, J. Org. Chem. 1975, 40, 3453.
18. G. W. Gribble, P. D. Lord, J. Skotnicki, S. E. Dietz, J. T. Eaton, J. L. Johnson, J. Am. Chem. Soc. 1974, 96, 7812; G. W. Gribble, P. W. Heald, Synthesis 1975, 650; P Marchini, G. Liso, A. Reho, J. Org. Chem. 1975, 40, 3453.
19. B. Tawil, A. Guggisberg, M. Hesse, Tetrahedron 1992, 48, 3775.
20. J. Song, Dissertation, Universität Zürich, 1993.
21. F A. Davis, O.D. Stringer, J. Org. Chem. 1982, 47, 1774; L.C. Vishwakarma, O.D. Stringer, F. A. Davis, Org. Synth. 1988, 66, 203.
22. F A. Davis, O.D. Stringer, J. Org. Chem. 1982, 47, 1774; L.C. Vishwakarma, O.D. Stringer, F. A. Davis, Org. Synth. 1988, 66, 203.
23. M. Díaz, H. Ripperger, Phytochemistry 1982, 21, 255.
24. E. Graf, H. Boeddeker, Anal. Chem. 1958, 613, 111
25. M. Diaz, A. Preiss, H. Rippberger, Phytochemistry 1987, 26, 1847.
26. S. Bashwira, C. Hootele, Tetrahedron 1988, 44, 4521.
27. R. E. Steiger, Org. Synth 1967, 3, 88.
28. D. Bormann, Chem. Ber. 1970, 103, 1797.
29. G. M. Sheldrick, Acta Crystallogr., Sect. A 1990, 46, 467
30. E. N. Maslen, A. G. Fox, M. A. O'Keefe, in 'International Tables for Crystallography', Ed. A. J. C. Wilson, Kluwer Academic Publishers, Dordrecht, 1992, Vol C, pp. 477-486.
31. R F. Stewart, E. R. Davidson, W. T. Simpson, J. Chem. Phys. 1965, 42, 3175.
32. J. A. Ibers, W. C. Hamilton, Acta Crystallogr. 1964, 17, 781.
33. D. C. Creagh, W. J. McAuley, in 'International Tables for Crystallography', Ed. A. J. C. Wilson, Kluwer Academic Publishers, Dordrecht, 1992, Vol C, pp. 219-222.
34. TEXSAN. Single Crystal Structure Analysis Software, Version 5.0, Molecular Structure Corporation, The Woodlands, Texas, 1989.