Total synthesis of (-)-galanthamine by remote asymmetric induction

Angewandte Chemie - International Edition

Volumn 43, Issue 20, 2004, Pages 2659-2661

  Kodama, Sumiaki ^a   Hamashima, Yoshio ^a   Nishide, Kiyoharu ^a   Node, Manabu ^a  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Alkaloids; Asymmetric synthesis; Michael addition; Natural products; Total synthesis

Indexed keywords

GALANTHAMINES; INTRAMOLECULAR REACTIONS;

ADDITION REACTIONS; ALCOHOLS; DERIVATIVES; SYNTHESIS (CHEMICAL);

AMINES;

ALCOHOL; ALLYL COMPOUND; DEXTRO PHENYLALANINE; GALANTAMINE; IMIDAZOLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; DERIVATIZATION; DRUG SYNTHESIS; MICHAEL ADDITION; SYNTHESIS;

GALANTAMINE; MODELS, CHEMICAL; MOLECULAR STRUCTURE; PARASYMPATHOMIMETICS; STEREOISOMERISM;

EID: 4544268833     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200353636     Document Type: Article

References (34)

1. a) O. Hoshino in The Alkaloids, Vol. 51 (Ed.: G. A. Cordell), Academic Press, New York, 1998, pp. 323-424;
2. b) S. F. Martin in The Alkaloids, Vol. 30 (Ed.: A. Brossi), Academic Press, New York, 1987, pp. 251-376.
3. R. L. Irwin, H. J. Smith III, Biochem. Pharmacol. 1960, 3, 147-148.
4. W.-C. Shieh, J. A. Carlson, J. Org. Chem. 1994, 59, 5463-5465.
5. a) L. Czollner, W. Frantsits, B. Küenburg, U. Hedenig, J. Fröhlich, U. Jordis, Tetrahedron Lett. 1998, 39, 2087-2088;
6. b) B. Küenburg, L. Czollner, J. Fröhlich, U. Jordis, Org. Process Res. Dev. 1999, 3, 425-431.
7. a) R. A. Holton, M. P. Sibi, W. S. Murphy, J. Am. Chem. Soc. 1988, 110, 314-316;
8. b) D. A. Chaplin, N. Fraser, P. D. Tiffin, Tetrahedron Lett. 1997, 38, 7931-7932;
9. c) D. A. Chaplin, N. B. Johnson, J. M. Paul, G. A. Potter, Tetrahedron Lett. 1998, 39, 6777-6780.
10. a) D. H. R. Barton, G. W. Kirby, Proc. Chem. Soc. London 1960, 392-393;
11. b) D. H. R. Barton, G. W. Kirby, J. Chem. Soc. 1962, 806-817;
12. c) T. Kametani, K. Yamaki, H. Yagi, K. Fukumoto, J. Chem. Soc. C 1969, 2602-2605;
13. d) K. Shimizu, K. Tomioka, S. Yamada, K. Koga, Heterocycles 1937, 8, 277-282;
14. e) K. Shimizu, K. Tomioka, S. Yamada, K. Koga, Chem. Pharm. Bull. 1938, 26, 3765-3771;
15. f) J. Szewczyk, A. H. Lewin, F. I. Carroll, J. Heterocycl. Chem. 1988, 25, 1809-1811;
16. g) R. Vlahov, D. Krikorian, G. Spassov, M. Chinova, I. Vlahov, S. Parushev, G. Snatzke, L. Ernst, K. Kieslich, W.-R. Abraham, W. S. Sheldrick, Tetrahedron 1989, 45, 3329-3345;
17. h) J. Szewczyk, J. W. Wilson, A. H. Lewin, F. I. Carroll, J. Heterocycl. Chem. 1995, 32, 195-199;
18. i) Y. Kita, M. Arisawa, M. Gyoten, M. Nakajima, R. Hamada, H. Tohma, T. Takada, J. Org. Chem. 1998, 63, 6625-6633.
19. a) B. M. Trost, F. D. Toste, J. Am. Chem. Soc. 2000, 122, 11262-11263;
20. b) B. M. Trost, W. Tang, Angew. Chem. 2002, 114, 2919-2921; Angew. Chem. Int. Ed. 2002, 41, 2795-2797;
21. b) B. M. Trost, W. Tang, Angew. Chem. 2002, 114, 2919-2921; Angew. Chem. Int. Ed. 2002, 41, 2795-2797;
22. for a synthesis of (±)-galanthamine, see: c) C. Guillou, J.-L. Beunard, E. Gras, C. Thal, Angew. Chem. 2001, 113, 4881-4882; Angew. Chem. Int. Ed. 2001, 40, 4745-4746;
23. for a synthesis of (±)-galanthamine, see: c) C. Guillou, J.-L. Beunard, E. Gras, C. Thal, Angew. Chem. 2001, 113, 4881-4882; Angew. Chem. Int. Ed. 2001, 40, 4745-4746;
24. for a synthesis of the galanthamine ring system, see: d) P. J. Parsons, M. D. Charles, D. M. Harvey, L. R. Sumoreeah, A. Shell, G. Spoors, A. L. Gill, S. Smith, Tetrahedron Lett. 2001, 42, 2209-2211;
25. e) C. Pilger, B. Westermann, U. Flöke, G. Fels, Synlett 2000, 1163-1165;
26. for a formal synthesis of (±)-lycoramine by the Heck reaction, see: f) E. Gras, C. Guillou, C. Thal, Tetrahedron Lett. 1999, 40, 9243-9244.
27. M. Node, S. Kodama, Y. Hamashima, T. Baba, N. Hamamichi, K. Nishide, Angew. Chem. 2001, 113, 3150-3152; Angew. Chem. Int. Ed. 2001, 40, 3060-3062.
28. M. Node, S. Kodama, Y. Hamashima, T. Baba, N. Hamamichi, K. Nishide, Angew. Chem. 2001, 113, 3150-3152; Angew. Chem. Int. Ed. 2001, 40, 3060-3062.
29. 2 computer system.
30. In the NOESY spectra of 6a and 6b a correlation was observed between the methine H atom at C5 and the ortho H atoms of the pyrogallol moiety at C2 of the imidazolidinone; see also: R. Naef, D. Seebach, Helv. Chim. Acta 1985, 68, 135-143.
31. S. Cacchi, P. G. Ciattini, E. Morera, G. Ortar, Tetrahedron Lett. 1986, 27, 5541-5544.
32. D = -131.4 (c = 0.6, EtOH): S. Y. Han, J. E. Sweeney, E. S. Bachman, E. J. Schweiger, G. Forloni, J. T. Coyle, B. M. Davis, M. M. Joullie, Eur. J. Med. Chem. 1992, 27, 673-687;
33. D = -112.8 (88% ee, c = 0.5, EtOH);[7a] c) [α]D = -123.1 (96% ee, c = 0.4, EtOH).[7b]
34. 2O (3.0 equiv), THF, room temperature, 2 h, 85% (2 steps).