Three-component biginelli cyclocondensation reaction using C-glycosylated substrates. Preparation of a collection of dihydropyrimidinone glycoconjugates and the synthesis of C-glycosylated monastrol analogues

Journal of Organic Chemistry

Volumn 67, Issue 20, 2002, Pages 6979-6994

  Dondoni, Alessandro ^a   Massi, Alessandro ^a   Sabbatini, Simona ^a   Bertolasi, Valerio ^a  

^a UNIVERSITY OF FERRARA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ASYMMETRIC INDUCTION;

ALDEHYDES; STEREOCHEMISTRY; SUBSTRATES; SUGAR (SUCROSE); SYNTHESIS (CHEMICAL); UREA; X RAY CRYSTALLOGRAPHY;

CONDENSATION REACTIONS;

3,4 DIHYDROPYRIMIDIN 2(1H) ONE DERIVATIVE; ALDEHYDE; DIHYDROPYRIDINE DERIVATIVE; DIHYDROPYRIMIDINE DERIVATIVE; ESTER; MONASTROL; NIFEDIPINE; REAGENT; SQ 32547; SQ 32926; UNCLASSIFIED DRUG; UREA;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; DIASTEREOISOMER; ENZYME GLYCOSYLATION; ENZYME SUBSTRATE; GLYCOSYLATION; PHARMACOPHORE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0037019968     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0202076     Document Type: Article

References (71)

1. Passerini three-component and Ugi four-component condensations are the most popular among many other reactions for their wide scope and synthetic utility. For reviews, see: (a) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. Eur. J. 2000, 6, 3321. (b) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168.
2. Passerini three-component and Ugi four-component condensations are the most popular among many other reactions for their wide scope and synthetic utility. For reviews, see: (a) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. Eur. J. 2000, 6, 3321. (b) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168.
3. (a) Dolle, R. E.; Nelson, K. H. J. Comb. Chem. 1999, 1, 235.
4. (b) Nuss, J. M.; Renhowe, P. A. Curr. Opin. Drug Discuss. Dev. 1999, 2, 631.
5. (c) Oliver, S. F.; Abell, C. Curr. Opin. Chem. Biol. 1999, 3, 299.
6. (d) Obrecht, D.; Villalgordo, J. M. In Solid-Supported Combinatorial and Parallel Synthesis of Small-Molecular-Weight Compounds Libraries; Baldwin, J. E., Williams, R. M., Eds.; Pergamon Press: New York, 1998.
7. (e) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555.
8. (f) Gordon, E. M.; Gallop, M. A.; Patel, D. V. Acc. Chem. Res. 1996, 29, 144.
9. Biginelli, P. Gazz. Chim. Ital. 1893, 23, 360.
10. For a review, see: Kappe, C. O. Tetrahedron 1993, 49, 6937.
11. Quite fairly, Biginelli stated (ref3) that his research was inspired by the earlier work of R. Behrend on the urea-ketoester coupling and U. Schiff on the urea-aldehyde coupling.
12. (a) Kappe, C. O. Acc. Chem. Res. 2000, 33, 879.
13. (b) Kappe, C. O. Bioorg. Med. Chem. Lett. 2000, 10, 49.
14. (c) Kappe, C. O.; Falsone, S. F.; Fabian, W. M. F.; Belaj, F. Heterocycles 1999, 51, 77.
15. (d) McDonald, A. I.; Overman, L. E. J. Org. Chem. 1999, 64, 1520.
16. (e) Kappe, C. O. J. Org. Chem. 1997, 62, 7201.
17. (f) Studer, A.; Jeger, P.; Wipf, P.; Curran, D. P. J. Org. Chem. 1997, 62, 2917.
18. (g) Wipf, P.; Cunningham, A. Tetrahedron Lett. 1995, 36, 7819.
19. (a) Kumar, K. A.; Kasthuraiah, M.; Reddy, C. S.; Reddy, C. D. Tetrahedron Lett. 2001, 42, 7873.
20. (b) Lu, J.; Bai, Y.; Wang, Z.; Yang, B.; Ma, H. Tetrahedron Lett. 2000, 41, 9075.
21. (c) Ranu, B. C.; Hajra, A.; Jana, U. J. Org. Chem. 2000, 65, 6270.
22. (d) Ma, Y.; Qian, C.; Wang, L.; Yang, M. J. Org. Chem. 2000, 65, 3864.
23. (e) Bigi, F.; Carloni, S.; Frullanti, B.; Maggi, R.; Sartori, G. Tetrahedron Lett. 1999, 40, 3465.
24. (f) Hu, E. H.; Sidler, D. R.; Dolling, U. H. J. Org. Chem. 1998, 63, 3454.
25. (g) Kappe, C. O.; Falsone, S. F. Synlett 1998, 718.
26. (a) Peng, J.; Deng, Y. Tetrahedron Lett. 2001, 42, 5917.
27. (b) Stadler, A.; Kappe, C. O. J. Chem. Soc., Perkin Trans. 2 2000, 1363.
28. Eisner, U.; Kuthan, J. Chem. Rev. 1972, 72, 1.
29. For an updated list of leading references on this topic, see: Jauk, B.; Belaj, F.; Kappe, C. O. J. Chem. Soc., Perkin Trans. 1 1999, 307.
30. Bossert, F.; Vater, W. US Pat. 3485847, 1969.
31. (a) Atwal, K. S.; Swanson, B. N.; Unger, S. E.; Floyd, D. M.; Moreland, S.; Hedberg, A.; O'Reilly, B. C. J. Med. Chem. 1991, 34, 806 and references therein.
32. (b) Atwal, K. S.; Rovnyak, G. C.; Kimball, S. D.; Floyd, D. M.; Moreland, S.; Swanson, B. N.; Gougoutas, J. Z.; Schwartz, J.; Smillie, K. M.; Malley, M. F. J. Med. Chem. 1990, 33, 2629.
33. For a survey on this topic with leading references, see: Kappe, C. O. Eur. J. Med. Chem. 2000, 35, 1043.
34. Mayer, T. U.; Kapoor, T. M.; Haggarty, S. J.; King, R. W.; Schreiber, S. L.; Mitchison, T. J. Science 1999, 286, 971.
35. For a preliminary report on this subject, see: Dondoni, A.; Massi, A.; Sabbatini, S. Tetrahedron Lett. 2001, 42, 4495.
36. (a) Fernàndez, M. V.; Herrera, F. J. L.; Cobos, T. L. Heterocycles 1988, 27, 2133.
37. (b) Fernàndez, M. V.; Herrera, F. J. L.; Cobos, T. L. Heterocycles, 1986, 24, 679.
38. (c) Sastre, J. A. L.; Molina, J. M. An. Quim. 1978, 74, 353.
39. Essentials of Glycobiology; Varki, A., Cummings, R., Esko, J., Freeze, H., Hart, G., Marth, J., Eds.; Cold Spring Harbor Laboratory Press: New York, 1999.
40. Varki, A. Glycobiology 1993, 3, 97.
41. For a recent report on the synthesis of new guanidine-sugars and leading references to earlier work on these glycoconjugates, see: Lin, P.; Lee, C. L.; Sim, M. M. J. Org. Chem. 2001, 66, 8243.
42. Postema, M. H. D. C-Glycoside Synthesis; CRC Press: Boca Raton, 1995; p 303.
43. (a) Hunziker, J.; Leumann, C. In Modern Synthetic Methods 1995; Ernst, B., Leumann, C., Eds.; VCH: Basel, 1995; p 333.
44. (b) Wilson, L. W.; Hager, M. W.; El-Kattan, Y. A.; Liotta, D. C. Synthesis 1995, 1465.
45. (c) Nucleosides and Nucleotides as Antitumor and Antiviral Agents; Chu, C. K., Baker, D. C., Eds.; Plenum Press: New York, 1993.
46. (d) Huryn, D. M.; Okabe, M. Chem. Rev. 1992, 92, 1745.
47. (e) Perigaud, C.; Gosselin, G.; Imbach, J.-L. Nucleosides Nucleotides 1992, 11, 903.
48. Schnell, B.; Krenn, W.; Faber, K.; Kappe, C. O. J. Chem. Soc., Perkin Trans. 1 2000, 4382.
49. (a) Dondoni, A. Pure Appl. Chem. 2000, 72, 1577.
50. (b) Dondoni, A.; Scherrmann, M.-C. J. Org. Chem. 1994, 59, 6404.
51. It has to be noted that the β-D-configured formyl C-ribofuranoside 5a was erroneously reported (ref 22b) to be the α-isomer. For a revision, see: Dondoni, A.; Formaglio, P.; Marra, A.; Massi, A. Tetrahedron 2001, 57, 7719.
52. Dhavale, D. D.; Bhujbal, N. N.; Joshi, P.; Desai, S. G. Carbohydr. Res. 1994, 263, 303.
53. The attachment of the sugar moiety to the urea through a methylene bridge was designed in order to ensure higher stability with respect to the N-glycosyl derivative.
54. Winkley, M. W. Carbohydr. Res. 1973, 31, 245.
55. (a) Togo, H.; Ishigami, S. Fujii, M.; Ikuma, T.; Yokoyama, M. J. Chem. Soc., Perkin Trans. 1 1994, 2931.
56. (b) Igarashi, Y.; Shiozawa, T.; Ichikawa, Y. Bioorg. Med. Chem. Lett. 1997, 7, 613 and references therein.
57. The use of catalytic CuCl as described in ref 7f afforded the Biginelli product in much lower yield (ca. 30%). It is likely that the presence of powdered 4-Å molecular sieves, acting as acid sponge, interfered with the action of the heterogeneous promoter.
58. (a) Krenn, W.; Verdino, P.; Uray, G.; Faber, K.; Kappe, C. O. Chirality 1999, 11, 659.
59. (b) Schnell, B.; Strauss, U. T.; Verdino, P.; Faber, K.; Kappe, C. O.Tetrahedron: Asymmetry 2000, 11, 1449.
60. (c) Kappe, C. O.; Shishkin, O. V.; Uray, G.; Verdino, P. Tetrahedron 2000, 56, 1859.
61. (d) Uray, G.; Verdino, P.; Belaj, F.; Kappe, C. O.; Fabian, W. M. F. J. Org. Chem. 2001, 66, 6685.
62. (a) Hansen, A. E.; Bouman, T. D. Adv. Chem. Phys. 1980, 44, 545.
63. (b) Ripa, L.; Hallberg, A.; Sandström, J. J. Am. Chem. Soc. 1997, 119, 5701.
64. It has to be noted that the assignment of the opposite configuration with respect to the ref 29d is due to the different substituent priorities.
65. Compound -17b was prepared by selective debenzylation of the corresponding O-benzyl ester which was in turn obtained by the standard cyclocondensation reaction using benzyl acetoacetate, urea, and the aldehyde 5b (see the Experimental Section).
66. Morelli, C. F.; Manferdini, M.; Veronese, A. C. Tetrahedron 1999, 55, 10803.
67. The phenolic hydroxy group was protected in order to avoid possible transesterification reactions by the O-benzoyl groups.
68. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
69. Ogawa, T.; Kikuchi, T.; Matsui, M.; Ohrui, H.; Kuzuhara, H.; Emoto, S. Agric. Biol. Chem. 1971, 35, 1825.
70. Dondoni, A.; Marra, A.; Massi, A. Tetrahedron 1998, 54, 2827.
71. Ambersep 900 OH was purchased from Fluka. This resin was washed with methanol and dried in vacuo before use.