Synthesis of bicyclic guanidines from pyrrolidin-2-one

Tetrahedron

Volumn 52, Issue 7, 1996, Pages 2629-2646

  Louwrier, Saskia ^a   Tuynman, Antonin ^a   Hiemstra, Henk ^a  

^a UNIVERSITY OF AMSTERDAM   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; GUANIDINE DERIVATIVE; PTILOMYCALIN A; PYRIMIDINE DERIVATIVE; PYRROLO[1,2 C]PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; X RAY DIFFRACTION;

EID: 0030066006     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)01086-6     Document Type: Article

References (63)

1. (a) Palagiano, E.; De Marino, S.; Minale, L.; Riccio, R.; Zollo, F.; Iorizzi, M.; Carré, J. B.; Debitus, C.; Lucarain, L.; Provost, J. Tetrahedron 1995, 51, 3675.
2. (b) Tavares, R.; Daloze, D.; Braekman, J. C.; Hadju, E.; Muricy, G.; Van Soest, R. W. M. Biochem. Syst. Ecol. 1994, 22, 645.
3. (c) Jares-Erijman, E. A.; Sakai, R.; Rinehart, K. L. J. Org. Chem. 1991, 56, 5712.
4. (d) Berlinck, R. G. S.; Braekman, J. C.; Daloze, D.; Bruno, I.; Riccio, R.; Ferri, S.; Spampinato, S.; Speroni, E. J. Nat. Prod. 1993, 56, 1007.
5. (e) Jares-Erijman, E. A.; Ingrum, A. L.; Carney, J. R.; Rinehart, K. L.; Sakai, R. J. Org. Chem. 1993, 58, 4805.
6. (f) Berlinck, R. G. S.; Braekman, J. C.; Daloze, D.; Hallenga, K.; Ottinger, R.; Bruno, I.; Riccio, R. Tetrahedron Lett. 1990, 31, 6531.
7. (g) Berlinck, R. G. S.; Braekman, J. C.; Daloze, D.; Bruno, I.; Riccio, R.; Rogeau, D.; Amade, P. J. Nat. Prod. 1993, 56, 528.
8. (h) Jares-Erijman, E. A.; Ingrum, A. A.; Sun, F.; Rinehart, K. L. J. Nat. Prod. 1993, 56, 2186.
9. (i) Patil, A. D.; Kumar, N. V.; Kokke, W. C.; Bean, M. F.; Freyer, A. J.; De Brosse, C.; Mai, S.; Truneh, A.; Faulkner, D. J.; Carte, B.; Breen, A. L.; Hertzberg, R. P.; Johnson, R. K.; Westley, J. W.; Potts, B. C. M. J. Org. Chem. 1995, 60, 1182.
10. (a) Guanidines: Historical, Biological, Biochemical, and Clinical Aspects of the Naturally Occuring Guanidino Compounds; Mori, A.; Cohen, B. D.; Lowenthal, A., Eds.; Plenum: New York, 1983. Guanidines 2: Further Explorations of the biological and clinical Significance of Guanidino Compounds; Mori, A.; Cohen, B. D.; Koide, H. Eds.; Plenum: New York, 1987.
11. (a) Guanidines: Historical, Biological, Biochemical, and Clinical Aspects of the Naturally Occuring Guanidino Compounds; Mori, A.; Cohen, B. D.; Lowenthal, A., Eds.; Plenum: New York, 1983. Guanidines 2: Further Explorations of the biological and clinical Significance of Guanidino Compounds; Mori, A.; Cohen, B. D.; Koide, H. Eds.; Plenum: New York, 1987.
12. (b) The Organic Chemistry of Drug Synthesis, Lednicer, D.; Mitscher, L. A.; Eds.; Wiley; New York, Vol. I (1977) and Vol. II (1980).
13. (a) Fink, M. L.; Bodanszky, M. J. Am. Chem. Soc. 1976, 98, 974.
14. (b) Dietrich, B. Fyles, D. L.; Lehn, J. M.; Pease, L. G.; Fyles, J. Chem. Soc. Chem. Commun. 1978, 934.
15. (c) Cotton, F. A.; Day, V. W.; Hazen, Jr. E. E.; Larsen, S. J. Am. Chem. Soc. 1973, 95, 4834.
16. Kashman, Y.; Hirsh, S.; McConnell, O. J.; Ohtani, I.; Kusumi, T.; Kakisawa, H. J. Am. Chem. Soc. 1989, 111, 8925.
17. (a) Ohtani, I.; Kusumi, T.; Kakisawa, H.; Kashman, Y.; Hirsh, S. J. Am. Chem. Soc. 1992, 114, 8472.
18. (b) Ohtani, I.; Kusumi, T.; Kakisawa, H. Tetrahedron Lett. 1992, 33, 2525.
19. (a) Overman, L. E.; Rabinowitz, M. H.; Renhowe, P. A. J. Am. Chem. Soc. 1995, 117, 2657.
20. (b) Overman, L. E.; Rabinowitz, M. H. J. Org. Chem. 1993, 58, 3235.
21. (c) Snider, B. B.; Shi, Z. Tetrahedron Lett. 1993, 34, 2099.
22. (d) Snider, B. B.; Shi, Z. J. Am. Chem. Soc. 1994, 116, 549.
23. (e) Murphy, P. J.; Williams, H. L.; Hursthouse, M. B.; Malik, K. M. A. J. Chem. Soc., Chem. Commun. 1994, 119.
24. (f) Murphy, P. J.; Williams, H. L. J. Chem. Soc., Chem. Commun. 1994, 819.
25. (g) Grillot, A. L.; Hart, D. J. Tetrahedron 1995, 51, 11377.
26. Louwrier, S.; Ostendorf, M.; Boom, A.; Hiemstra, H.; Speckamp, W. N., preceding paper in this issue.
27. (a) Somfai, P.; Åhman, J. Tetrahedron Lett. 1992, 33, 3791.
28. (b) Åhman, J.; Somfai, P. Tetrahedron 1992, 48, 9537.
29. Shono, T.; Matsumura, Y.; Tsubata, K. J. Am. Chem. Soc. 1981, 103, 1172.
30. Shono, T.; Matsumura, Y.; Uchida, K.; Tsubata, K.; Makino, A. J. Org. Chem. 1984, 49, 300.
31. Sakaitani, M.; Hori, K.; Ohfune, Y. Tetrahedron Lett. 1988, 29, 2984.
32. (a) Bernatowicz, M. S.; Wu, Y.; Matsueda, G. R. J. Org. Chem. 1992, 57, 2497.
33. (b) Bernatowicz, M. S.; Wu, Y.; Matsueda, G. R. Tetrahedron Lett. 1993, 34, 3389.
34. (c) Drake, B.; Patek, M.; Lebl, M. Synthesis 1994, 579.
35. (d) Verdini, A. S.; Lucietto, P.; Fossati, G.; Giordiani, C. Tetrahedron Lett. 1992, 33, 6541.
36. (e) For the corresponding bis-methoxycarbonyl derivative see: Shawkat Naim, S.; Sharma, S. Synthesis 1992, 664.
37. (f) Bergeron, R. J.; McManis, J. S. J. Org. Chem. 1987, 52, 1700.
38. (g) Poss, M. A.; Iwanowicz, E.; Reid, J. A.; Lin, J.; Gu, Z. Tetrahedron Lett. 1992, 33, 5933.
39. (h) Kim, K. S.; Qian, L. Tetrahedron Lett. 1993, 34, 7677.
40. (i) Kim, K. S.; Qian, L. Tetrahedron Lett. 1993, 34, 7195.
41. (a) Snider, B. B.; Faith, W. C. Tetrahedron Lett. 1983, 24, 861.
42. (b) Snider, B. B.; Faith, W. C. J. Am. Chem. Soc. 1984, 106, 1443.
43. A Michael reaction can be reversible: Jung, M. E. in Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, Vol. 4, Chapter 1.1 (pp 3).
44. For other retro-Michael reactions see: (a) Collins, D. J.; Fallon, G. D.; Skene, C. E. Aust. J. Chem. 1994, 47, 649.
45. (b) Kitano, K.; Katagiri, N.; Kaneko, C. Chem. Lett. 1994, 1285.
46. A Mannich reaction can be reversible: (a) Tramontini, M. Synthesis 1973, 703.
47. (b) Tramontini, M.; Angiolini, L. Tetrahedron 1990, 46, 1791.
48. For other retro-Mannich reactions see: (a) Arai, H.; Kasai, M. J. Org. Chem. 1994, 59, 1087.
49. (b) Schleimer, R.; Würthwein, E. U. Chem. Ber. 1994, 127, 1427.
50. (c) Feldman, P. L.; Rapoport, H. J. Org. Chem. 1986, 51, 3882.
51. Gribble, G. W.; Nutaitis, C. F. Org. Prep. Proc. Int. 1985, 17, 317.
52. (a) Mancuso, A. J.; Huang, S. L.; Swern, D. J. Org. Chem. 1978, 43, 2480.
53. (b) Mancuso, A. J.; Swern, D. Synthesis 1981, 165.
54. (a) Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639.
55. (b) Taylor, E. C.; Ahmed, A. J. Org. Chem. 1991, 56, 5443.
56. (c) Griffith, W. P.; Ley, S. V.; Whitecombe, G. P.; White, A. D. J. Chem. Soc., Chem. Commun. 1987, 1625.
57. (a) Meyer, S. D.; Schreiber, S. L. J. Org. Chem. 1994, 59, 7549.
58. (b) Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
59. (c) Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277.
60. (d) Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4156.
61. Frigerio, M.; Santagostino, M. Tetrahedron Lett. 1994, 43, 8019.
62. Iwanowicz, E. J.; Poss, M. A.; Lin, J. Synth. Commun. 1993, 23, 1443.
63. Experimental details of the X-ray structure determinations, ORTEP representations and tables of fractional atomic coordinates, thermal parameters, interatomic distances and angles for 34a and 39a were deposited by the Editor at the Cambridge Crystallographic Data Centre.