Studies on the synthesis of Strychnos indole alkaloids from 2-(3-indolyl)piperidine derivatives. A new synthetic entry to the indolo[3,2-a]quinolizidine system

Arkivoc

Volumn 2004, Issue 4, 2004, Pages 14-25

  Amat, Mercedes ^a   Llor, Nuria ^a   Coll, Ma Dolors ^a   Casamitjana, Nuria ^a   Bosch, Joan ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

Electrophilic substitution on indoles; Indoloquinolizidine; Palladium(0) cross coupling; Pummerer reaction; Strychnos alkaloids

Indexed keywords

2 (3 INDOLYL)PIPERIDINE 4 ACETATE; 5 (1 ACETOXYETHYL) 2 (3 INDOLYL)PYRIDINE; 5 (1 HYDROXYETHYL) 2 (3 INDOLYL)PYRIDINE; INDOLE ALKALOID; INDOLO[3,2 A]QUINOLIZIDINE DERIVATIVE; METHYL 3 ETHYLIDENE 8 (METHOXYCARBONYL) 7 (PHENYLSULFANYL)INDOLO[3,2 A]QUINOLIZIDINE 2 ACETATE; METHYL 5 ETHYLIDENE 2 [1 (METHOXYCARBONYL) 3 INDOLYL] 1 [2 (PHENYLSULFINYL)ETHYL] 4 PIPERIDINE ACETATE; PIPERIDINE DERIVATIVE; PYRIDINE DERIVATIVE; QUINOLIZIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CIS TRANS ISOMERISM; CROSS COUPLING REACTION; DEBENZYLATION; DESILYLATION; HYDROGENATION; METHANOLYSIS; PUMMERER REACTION; REACTION ANALYSIS; RING CLOSING METATHESIS; STEREOISOMERISM; STRYCHNOS; SYNTHESIS;

EID: 2942666281     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (49)

1. a) Amat, M.; Llor, N.; Pshenichnyi, G.; Bosch, J. ARKIVOC 2002, 3, 73;
2. b) Amat, M.; Seffar, F.; Llor, N.; Bosch, J. Synthesis 2001, 267;
3. c) Amat, M.; Hadida, S.; Pshenichnyi, G.; Bosch, J. J. Org. Chem. 1997, 62, 3158, and references cited therein.
4. a) Bosch, J.; Bonjoch, J.; Amat, M. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, 1996; Vol. 48, Chapter 2;
5. b) Sapi, J.; Massiot, G. In Monoterpenoid Indole Alkaloids; Saxton, J. E., Ed. In The Chemistry of Heterocyclic Compounds; Taylor, E. C., Ed.; Wiley: Chichester, 1994; Supplement to Vol. 25, Part 4, Chapter 7;
6. Husson, H.-P. In The Monoterpenoid Indole Alkaloids; Saxton, J. E., Ed. In The Chemistry of Heterocyclic Compounds; Weissberger, A.; Taylor, E. C., Eds.; Wiley: Chichester, 1983; Vol. 25, Part 4, Chapter VII.
7. Amat, M.; Bosch, J. J. Org. Chem. 1992, 57, 5792.
8. For the use of TMSOTf as initiator of Pummerer reactions, see: a) García-Ruano, J. L.; García-Paredes, C. Tetrahedron Lett. 2000, 41, 261;
9. b) Padwa, A.; Waterson, A. G. Tetrahedron 2000, 56, 10159;
10. c) Craig, D.; Daniels, K.; MacKenzie, A. R. Tetrahedron 1992, 48, 7803, and references cited therein.
11. For a review on the use of the Pummerer reaction in the synthesis of heterocycles, see: a) Padwa, A.; Gunn, D. E., Jr.; Osterhout, M. H. Synthesis 1997, 1353.
12. For other reviews, see: b) DeLucchi, O.; Miotti, U.; Modena, G. Organic Reactions 1991, 40, 157;
13. c) Grierson, D. S.; Husson, H.-P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 6, pp 907-947;
14. Kennedy, M.; McKervey, M. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 7, pp 193-216.
15. a) Emde, H.; Simchen, G. Liebigs Ann. Chem. 1983, 816.
16. See also: b) Brownbridge, P. Synthesis 1983, 1;
17. Brownbridge, P. Synthesis 1983, 85.
18. a) Remers, W. A. In Indoles; Houlihan, W. J., Ed. In The Chemistry of Heterocyclic Compounds; Weissberger, A.; Taylor, E. C., Eds.; Wiley: New York, 1972; Part 1, Chapter I;
19. b) Sundberg, R. J. The Chemistry of Indoles; Blomquist, A. T., Ed.; Academic Press: New York, 1970; Chapter I.
20. a) Biswas, K. M.; Jackson, A. H. Tetrahedron 1969, 25, 227;
21. b) Jackson, A. H.; Naidoo, B.; Smith, P. Tetrahedron 1968, 24, 6119;
22. c) Jackson, A. H.; Smith, P. Tetrahedron 1968, 24, 2227.
23. a) Cox, E. D.; Cook, J. M. Chem. Rev. 1995, 95, 1797;
24. b) Kowalski, P.; Bojarski, A. J.; Mokrosz, J. L. Tetrahedron 1995, 51, 2737, and references cited therein.
25. a) Frost, J. R.; Gaudillière, B. R. P.; Kauffmann, E.; Loyaux, D. ; Normand, N.; Petry, G.; Poirier, P.; Wenkert, E.; Wick, A. E. Heterocycles 1989, 28, 175;
26. b) Biswas, K. M.; Dhara, R. N.; Halder, S.; Mallik, H.; Sinha-Chaudhuri, A.; De, P.; Brahmachari, A. S. Synth. Commun. 1993, 23, 379.
27. For a review: a) Ungemach, F.; Cook, J. M. Heterocycles 1978, 9, 1089.
28. See also: b) Ganesan, A.; Heathcok, C. H. Tetrahedron Lett. 1993, 34, 439;
29. c) Curness, K.; Dyke, S. Heterocycles 1979, 12, 1133.
30. For mechanistic studies in the context of the synthesis of eudistomins, see: a) Liu, J.-J.; Hino, T.; Tsuruoka, A.; Harada, N.; Nakagawa, M. J. Chem. Soc., Perkin Trans. 1 2000, 3487;
31. b) van Maarseveen, J. H.; Scheeren, W.; Kruse, C. G. Tetrahedron 1993, 49, 2325;
32. c) Kawate, T.; Nakagawa, M.; Ogata, K.; Hino, T. Heterocycles 1992, 33, 801;
33. d) Liu, J.; Nakagawa, M.; Ogata, K.; Hino, T. Chem. Pharm. Bull. 1991, 39, 1672;
34. e) Liu, J.; Nakagawa, M.; Hino, T. Tetrahedron 1989, 45, 7729;
35. Nakagawa, M.; Liu, J.; Ogata, K.; Hino, T. J. Chem. Soc., Chem. Commun. 1988, 463.
36. For the intramolecular trapping of the indolenine intermediate by enol or enolates, see: g) Turet, L.; Markó, I. E.; Tinant, B.; Declercq, J.-P.; Touillaux, R. Tetrahedron Lett. 2002, 43, 6591;
37. h) England, D. B.; Kuss, T. D. O.; Keddy, R. G.; Kerr, M. J. Org. Chem. 2001, 66, 4704;
38. i) Bobowski, G.; Morrison, G. C. J. Org. Chem. 1981, 46, 4927;
39. j) Garnick, R. L.; Levery, S. B.; Le Quesne, P. W. J. Org. Chem. 1978,43, 1226;
40. k) Büchi, G.; Matsumoto, K. E.; Nishimura, H. J. Am. Chem. Soc. 1971, 93, 3299.
41. For the intramolecular trapping of the indolenine intermediate by an allylsilane, see: l) He, F.; Bo, Y.; Altom, J. D.; Corey, E. J. J. Am. Chem. Soc. 1999, 121, 6771.
42. For the intramolecular trapping of the spiroindoleninium salt generated in a Pummerer reaction from a 3-substituted indole, see: Oikawa, Y.; Yonemitsu, O.J. Org. Chem. 1976,41, 1118.
43. Diez, A.; Vila, C.; Sinibaldi, M.-E.; Troin, Y.; Rubiralta, M. Tetrahedron Lett. 1993,34, 733.
44. For reviews, see: a) Rhoads, S. J.; Raulins, N. R. Org. React. 1975, 22, 1;
45. Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M., Ed., Pergamon Press; Oxford, 1991. Vol. 5, Chapter 7.
46. This stereochemical issue did not concern us unduly because the reversibility of spiroindolenine intermediates related to B (Figure 1) through the corresponding iminium salts has been postulated: Melnyk, P.; Ducrot, P.; Thal, C. Tetrahedron 1993,49, 8589, and references cited therein.
47. Casnati, G.; Dossena, A.; Pochini, A.Tetrahedron Lett. 1972, 5277.
48. a) Wenkert, E.; Shi, Y.-J. Synth. Commun. 1989, 19, 1071;
49. Finch, N.; Gemenden, C. W.; Hsu, I. H.-C.; Kerr, A.; Sim, G. A.; Taylor, W. I.J. Am. Chem. Soc. 1965, 87, 2229.