A new synthetic entry to the indolo[2,3-a]quinolizidine system. Electrophilic cyclizations on the indole ring from 2-(2-piperidyl)indoles

Tetrahedron Letters

Volumn 37, Issue 17, 1996, Pages 3071-3074

  Amat, Mercedes ^a   Hadida, Sabine ^a   Sathyanarayana, Swargam ^a   Bosch, Joan ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE; INDOLO[2,3 O]QUINOLIZIDINE DERIVATIVE; QUINOLIZIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030000558     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00472-8     Document Type: Article

References (29)

1. (a) Kisakürek, M. V.; Leeuwenberg, A. J. M.; Hesse, M. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; John Wiley and Sons: New York, 1983; Vol. 1, Chapter 5.
2. (b) Attaur-Rahman; Basha, A. Biosynthesis of Indole Alkaloids; Clarendon Press: Oxford, 1983.
3. (a) Brown, R. T. In Indoles, The Monoterpenoid Indole Alkaloids; Saxton, J. E., Ed. in The Chemistry of Heterocyclic Compounds ; Weissberger, A.; Taylor, E. C., Eds.; John Wiley and Sons: New York, 1983; Vol. 25, Part 4, Chapter 3.
4. (a) Brown, R. T. In Indoles, The Monoterpenoid Indole Alkaloids; Saxton, J. E., Ed. in The Chemistry of Heterocyclic Compounds ; Weissberger, A.; Taylor, E. C., Eds.; John Wiley and Sons: New York, 1983; Vol. 25, Part 4, Chapter 3.
5. (a) Brown, R. T. In Indoles, The Monoterpenoid Indole Alkaloids; Saxton, J. E., Ed. in The Chemistry of Heterocyclic Compounds ; Weissberger, A.; Taylor, E. C., Eds.; John Wiley and Sons: New York, 1983; Vol. 25, Part 4, Chapter 3.
6. (b) Saxton, J. E. Ibid, Chapter 9.
7. (c) Lounasmaa, M.; Tolvanen, A. In Monoterpenoid Indole Alkaloids; Saxton, J. E., Ed. in The Chemistry of Heterocyclic Compounds Taylor, E. C., Ed.; John Wiley and Sons: Chichester, 1994; Vol. 25, Supplement to Part 4, Chapter 3.
8. (c) Lounasmaa, M.; Tolvanen, A. In Monoterpenoid Indole Alkaloids; Saxton, J. E., Ed. in The Chemistry of Heterocyclic Compounds Taylor, E. C., Ed.; John Wiley and Sons: Chichester, 1994; Vol. 25, Supplement to Part 4, Chapter 3.
9. (c) Lounasmaa, M.; Tolvanen, A. In Monoterpenoid Indole Alkaloids; Saxton, J. E., Ed. in The Chemistry of Heterocyclic Compounds Taylor, E. C., Ed.; John Wiley and Sons: Chichester, 1994; Vol. 25, Supplement to Part 4, Chapter 3.
10. (d) Szántay, C. Ibid, Chapter 9.
11. (a) Rubiralta, M.; Diez, A.; Bosch, J.; Solans, X. J. Org. Chem. 1989, 54, 5591.
12. (b) For further examples of this type of cyclization, see: Rubiralta, M.; Diez, A.; Vila, C. Tetrahedron 1990, 46, 4443.
13. (c) For a related approach involving the use of 3-(2-piperidyl)indole derivatives followed by rearrangement of the intermediate spiroindolenine, see: Diez, A.; Vila, C.; Sinibaldi, M.-E.; Troin, Y.; Rubiralta, M. Tetrahedron Lett. 1993, 34, 733.
14. Amat, M.; Hadida, S.; Bosch, J. Tetrahedron Lett. 1993, 34, 5005.
15. All yields are from material purified by column chromatography. Satisfactory analytical and/or spectral data were obtained for all new compounds.
16. 3O); 54.6 (CH); 57.2 (C-2); 98.6 (C-3'); 110.9 (C-7'); 119.7 (C-4'); 120.4 (C-5'); 121.6 (C-6'); 128.0 (C-3'a); 136.0 (C-7'a); 141.0 (C-2'); 168.8 (2 C=O). Picrate: m.p. 156-158°C (EtOH).
17. (a) De Lucchi, O.; Miotti, U.; Modena, G. Org. React. 1991, 40, 157.
18. (b) Grierson, D. S.; Husson, H.-P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 6, Chapter 4.7.
19. (c) Kennedy, M.; McKervey, M. A. Ibid, Vol. 7, Chapter 2.4.
20. Oikawa, Y.; Yonemitsu, O. J. Org. Chem. 1976, 41, 1118.
21. (a) Gallagher, T.; Magnus, P.; Huffman, J. C. J. Am. Chem. Soc. 1983, 105, 4750.
22. (b) Amat, M.; Bosch, J. J. Org. Chem. 1992, 57, 5792.
23. There are few examples of the Pummerer reaction from β-amino sulfoxides: (a) Takano, S.; Iida, H.; Inomata, K.; Ogasawara, K. Heterocycles 1993, 35, 47.
24. (b) Catena, J.; Valls, N.; Bosch, J.; Bonjoch, J. Tetrahedron Lett. 1994, 35, 4433. See also reference 9b. For similar N-dealkylations of β-amino sulfoxides under the Pummerer reaction conditions, see reference 9b.
25. 3) 6 27.8 (C-3); 33.6 (C-1); 36.9 (C-2); 42.7 (C-7); 52.4 (MeO); 53.8 (MeO); 54.5 (C-6); 55.7 (C-4); 57.4 (CH); 59.1 (C-12b); 115.3 (C-11); 119.7 (C-8); 123.1 (C-9); 124.5 (C-10); 127.3 (C-p); 128.8 (C-o); 132.9 (C-m); 151.9 (C=O); 168.7 (C=O).
26. For the use of this strategy in the construction of the seven-membered C ring of Iboga alkaloids, see: (a) Sundberg, R. J.; Amat, M.; Fernando, A. J. Org. Chem. 1987, 52, 3151.
27. (b) Sundberg, R. J.; Gadamasetti, K. G. Tetrahedron 1991, 47, 5673.
28. 3); 54.5 (C-4); 56.7 (CH); 59.3 (C-12b); 61.5 (C-6); 62.0 (C-7); 110.8 (C-7a); 111.1 (C-11); 118.4 (C-8); 120.0 (C-9); 121.8 (C-10); 126.2 (C-7b); 136.0 (C-12a); 136.5 (C-11a); 168.7 (C=O).
29. Grierson, D. S.; Vuilhorgne, M.; Husson, H.-P.; Lemoine, G. J. Org. Chem. 1982, 47, 4439.