Tandem carbophilic addition-N-acyliminium ion cyclization for the synthesis of functionalized pyrrolo[2,1-a]isoquinolones: Key intermediate for the preparation of Erythrina-type alkaloids

Tetrahedron Letters

Volumn 37, Issue 43, 1996, Pages 7841-7844

  Manteca, Izaskun ^a   Sotomayor, Nuria ^a   Villa, María Jesús ^a   Lete, Esther ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ISOQUINOLINE DERIVATIVE; PYRROLO[2,1 A]ISOQUINOLINE DERIVATIVE;

ARTICLE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

BETULACEAE;

EID: 0030597180     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01745-5     Document Type: Article

References (29)

1. 1. Reviews: (a) Speckamp, W. N. Rec. Trav. Chim. Pays-Bas 1981,100, 345-354.
2. (b) Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367-4416.
3. (c) Hiemstra, H.; Speckamp, W. N. In The Alkaloids; Academic Press: New York, 1988; vol. 32, pp. 271-339.
4. (d) Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I. Eds.; Pergamon Press: Oxford, 1991; vol. 2; pp. 1047-1082.
5. (e) Maryanoff, B. E.; Rebarchak, M. C. Synthesis 1992, 1245-1248 and references therein.
6. 2. For representative examples of π-nucleophiles, see: ref 1. For some recent examples, see: (a) Heaney, H.; Shuhaibar, K. F. Synlett 1995, 47-48.
7. (b) Lee, Y, S.; Kang, D. W.; Lee, S. J.; Park, H. J. Org. Chem. 1995, 60, 7149-7152.
8. (c) Li, W. H.; Hanau, C. E.; Davignon, A.; Moeller, K. D. J. Org. Chem. 1995, 60, 8155-8170.
9. (d) Logers, M.; Overman, L. E.; Welmalker, G. S. J. Am. Chem. Soc. 1995, 117, 9139-9150.
10. (e) Marson, C. M.; Pink, J. H.; Smith, C. Tetrahedron Lett. 1995, 36, 8107-8110.
11. (f) Rigo, B.; Elghammarti, S.; Couturier, D. Tetrahedron Lett. 1996, 37, 485-486.
12. (g) Yamada, H.; Aoyagi, S.; Kibayashi, C. J. Am. Chem. Soc. 1996,118, 1054-1059.
13. 3. Lete, E.; Egiarte, A.; Sotomayor, N.; Vicente, T.; Villa, M. J. Synlett, 1993, 41-43.
14. 4. (a) Collado, M. I.; Lete, E.; Sotomayor, N.; Villa, M. J. Tetrahedron 1995, 51, 4701-4710.
15. (b) Collado, M. I.; Sotomayor, N.; Villa, M. J.; Lete, E. Tetrahedron Lett. 1996, in press.
16. 5. Bentley, K. W. Nat. Prod. Rep. 1994,11, 555-576 and refences cited therein.
17. 6. (a) Hanessian, S.; Gomtsyan, A.; Payne, A. Hervé, Y.; Beaudoin, S. J. Org. Chem. 1993, 58, 5032-5034.
18. (b) Meyers, A. I.; Snyder, L. J. Org. Chem. 1992, 57, 3814-3819.
19. 7. Seyferth, D.; Weiner, M. A. J. Org. Chem. 1961, 26, 4797-4800.
20. 8. Maryanoff, D. F.; McComsey, D. F.; Dhul-Emswiler, B. A. J. Org. Chem. 1983, 48, 5062-5074.
21. 9. (a) Brook, A. G. Acc. Chem. Res. 1974, 7, 77-84.
22. (b) Hudrlick, P. F.; Peterson, D.; Rona, R. J. J. Org. Chem. 1975, 40, 2263-2264.
23. (c) Tietze, L. F.; Geisler, H.; Gewert, J. A.; Jacobi, U. Synlett 1994, 511-512.
24. 10. N-[(3,4-dimethoxyphenyl)]ethylmaleimide and N-[(3,4-dimethoxyphenyl)]ethyl-cis-norbor-5-en-2,3-dicarboximide (7) were prepared by condensation of the N-(3,4-dimethoxyphenyl)ethylamine with the corresponding anhydride in refluxing acetic acid.
25. 11. Heilmann, S. M.; Rasmussen, J. K. W. N. In Comprehensive Heterocyclic Chemistry, Katritzsky, A. R.; Rees, C. W.; Meth-Cohn, O. Eds.; Pergamon Press: Oxford, 1984; vol. 1; pp. 269-346.
26. 12. α-Lithium dithianes have been reported to give 1,4 conjugated additions: (a) Schultz, A. G. Yee, Y. K. J. Org. Chem. 1976, 41, 4044-4045.
27. (b) Prodger, J. C.; Bulmann Page, P. C.; van Niel M. B. Tetrahedron 1989, 45, 7643-7677.
28. (c) Forns, P.; Díez, A.; Rubiralta, M.; Solans, X.; Font-Bardia, M. Tetrahedron, 1996, 52, 3563-3574.
29. 13. Cohen, T.; Bhupathy, M. Acc. Chem. Res. 1989, 22, 52-161, and references therein.