An expedient strategy for the synthesis of tryptamines and other heterocycles

Angewandte Chemie - International Edition

Volumn 47, Issue 22, 2008, Pages 4217-4220

  Nicolaou, K C ^a,b,c   Krasovskiy, Arkady ^a,b   Trépanier, Vincent É ^a,b   Chen, David Y K ^c  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c INSTITUTE OF CHEMICAL AND ENGINEERING SCIENCES   (Singapore)

Author keywords

Heterocycles; Indoles; Metalation; Synthetic methods; Tryptamines

Indexed keywords

KETONES;

HETEROCYCLES; INDOLES; METALATION; SYNTHETIC METHODS; TRYPTAMINES;

CHEMICAL REACTIONS;

TRYPTAMINE DERIVATIVE;

ARTICLE; SYNTHESIS; TECHNIQUE;

METHODS; TRYPTAMINES;

EID: 47049108949     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200800404     Document Type: Article

References (31)

1. K. C. Nicolaou, D. J. Edmonds, P. G. Bulger, Angew. Chem. 2006, 118, 7292-7344;
2. Angew. Chem. Int. Ed. 2006, 45, 7134-7186.
3. For use of the tert-butoxycarbonyl moiety as an ortho-directing group in arene metalations, see: a) P. Stanetty, H. Koller, M. Mihovilovic, J. Org. Chem. 1992, 57, 6833-6837;
4. b) J. N. Reed, V. S. Snieckus, Tetrahedron Lett. 1984, 25, 5505-5508;
5. The original procedure from J. M. Muchowski, M. C. Venuti, J. Org. Chem. 1980, 45, 4798-4801 gave, in our hands, repeatedly low yields.
6. For the metalation of N-Boc pyrrolidines, see: a) P. Beak, D. B. Reitz, Chem. Rev. 1978, 78, 275-316;
7. b) P. Beak, W. J. Zajdel, D. B. Reitz, Chem. Rev. 1984, 84, 471-523;
8. c) D. J. Gallagher, P. Beak, J. Org. Chem. 1995, 60, 7092-7093;
9. d) K. M. B. Gross, P. Beak, J. Am. Chem. Soc. 2001, 123, 315-321.
10. For an elegant use of such an enamine derivative in total synthesis, see: V. H. Rawal, S. Iwasa, J. Org. Chem. 1994, 59, 2685-2686.
11. For the synthesis and biological activity of tryptamines, see: a) A. Shulgin, A. Shulgin, PIHKAL, Transform Press, Berkeley, CA, USA, 1991;
12. b) R. J. Sundberg, Indoles, Best Synthetic Methods Series, Academic Press, London, 1996;
13. c) S. Freeman, J. F. Alder, J. Med. Chem. 2002, 37, 527-539.
14. A. Krasovskiy, F. Kopp, P. Knochel, Angew. Chem. 2006, 118, 511-515;
15. Angew. Chem. Int. Ed. 2006, 45, 497-500.
16. J. C. Barrow, P. G. Nantermet, H. G. Selnick, K. L. Glass, P. L. Ngo, M. B. Young, J. M. Pellicore, M. J. Breslin, J. H. Hutchinson, R. M. Freidinger, C. Condra, J. Karczewski, R. A. Bednar, S. L. Gaul, A. Stern, R. Gould, T. M. Connolly, Bioorg. Med. Chem. Lett. 2001, 11, 2691-2696.
17. Since it was more convenient to transfer small amounts of TIPSCl than TBSCl under inert atmosphere, the former was favored throughout this work.
18. CCDC 675373 (1c) and 675374 (1d) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/ data_request/cif.
19. a) F. Yamada, M. Tamura, A. Hasegawa, M. Somei, Chem. Pharm. Bull. 2002, 50, 92-99;
20. b) F. Yamada, M. Tamura, M. Somei, Heterocycles 1998, 49, 451-457;
21. c) H. Sakagami, K. Ogasawara, Heterocycles 1999, 51, 1131-1135;
22. d) D. E. Nichols, S. Frescas, Synthesis 1999, 935-938.
23. a) A. Stoll, F. Troxler, J. Peyer, A. Hofmann, Helv. Chim. Acta 1955, 38, 1452-1472;
24. b) A. Hofmann, R Heim, A. Brack, H. Kobel, A. Frey, H. Ott, T. Petrzilka, F. Troxler, Helv. Chim. Acta 1959, 42, 1557-1572;
25. c) R. W. Brimblecombe, R. M. Pinder, Hallucinogenic Agents, Wright-Scientechnica, Bristol, 1975, pp. 106-108.
26. F. He, Y. Bo, J. D. Altom, E. J. Corey, J. Am. Chem. Soc. 1999, 121, 6771-6772.
27. H.-J. Knölker, T. Braxmeier, G. Schlechtingen, Angew. Chem. 1995, 107, 2746-2749;
28. Angew. Chem. Int. Ed. Engl. 1995, 34, 2497-2500.
29. J. M. Mejia-Oneto, A. Padwa, Org. Lett. 2006, 8, 3275-3278.
30. A. Krasovskiy, P. Knochel, Angew. Chem. 2004, 116, 3396-3399;
31. Angew. Chem. Int. Ed. 2004, 43, 3333-3336.