Highly diastereoselective 1,3-dipolar cycloaddition of a D-galactose-derived nitrone with dimethyl maleate: Synthesis of polyhydroxylated perhydroazaazulenes

Synlett

Volumn , Issue 12, 2009, Pages 1959-1963

  Bande, Omprakash P ^a   Jadhav, Vrushali H ^a   Puranik, Vedavati G ^b   Dhavale, Dilip D ^a  

^a UNIVERSITY OF PUNE   (India)

^b NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

1,3 dipolar nitrone olefin cycloaddition (DNOC); Diastereoselectivity; Iminosugars; Inhibitors; Nitrone

Indexed keywords

AMPHOLYTE; AZULENE DERIVATIVE; CITRACONIC ACID; DIMETHYLMALEATE; GALACTOSE; HEXAHYDROXYPERHYDROAZAAZULENE DERIVATIVE; ISOXAZOLIDINE DERIVATIVE; LACTAM; NITRONE; PENTAHYDROXYPERHYDROAZAAZULENE DERIVATIVE; POLYHYDROXYLATED PERHYDROAZAAZULENE DERIVATIVE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; CYCLOADDITION; DIASTEREOISOMER; STEREOCHEMISTRY; SYNTHESIS;

EID: 67849093833     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1217541     Document Type: Article

References (80)

1. (a) Pellissier, H. Tetrahedron 2007, 63, 3235.
2. (b) Ruck-Braun, K.; Tonia, H. E.; Wierschem, F. Chem. Soc. Rev. 2005, 34, 507.
3. (c) Gothelf, K. V.; Jorgensen, K. A. Chem. Rev. 1998, 98, 863.
4. (d) Confalone, P. N.; Huie, E. M. Org. React. 1988, 36, 1.
5. (e) Torseel, K. B. G. Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis; Feuer, H., Ed.; VCH: Weinheim, 1988.
6. (f) Ferrier, R. J.; Middleton, S. Chem. Rev. 1993, 93, 2779.
7. (g) Osborn, H. M.; Gemmell, N.; Harwood, L. M. J. Chem Soc., Perkin Trans. 1 2002, 2419.
8. (h) Frederickson, M. Tetrahedron 1997, 53, 403.
9. (i) Adams, J. P.; Box, D. S. J. Chem. Soc., Perkin Trans. 1 1999, 749.
10. (j) Karlsson, S.; Hogberg, H. E. Org. Prep. Proced. Int. 2001, 33, 103.
11. (k) Koumbis, A. E.; Gallos, J. K. Curr. Org. Chem. 2003, 7, 585.
12. (l) STD#§l)Padwa, A.; Pearson, W. H. J. Nat. Prod. 2004, 67, 1074.
13. (m) Padwa, A.; Pearson, W. H. Org. Process Res. Dev. 2004, 8, 293.
14. (n) Padwa, A.; Pearson, W. H. J. Am. Chem. Soc. 2002, 124, 12633.
15. (o) Cycloaddition Reactions in Organic Synthesis, Vol. 8; Carruthers, W., Ed.; Tetrahedron Organic Chemistry Series, Pergamon Press: New York, 1990, 269.
16. (p) Advances in Cycloaddition, Vol. 1; Curran, D. P., Ed.; JAI Press: London, 1988.
17. (q) Advances in Cycloaddition, Vol. 2; Curran, D. P., Ed.; JAI Press: London, 1990.
18. (r) Advances in Cycloaddition, Vol. 3; Curran, D. P., Ed.; JAI Press: London, 1993.
19. (s) Gothelf, K. V. In Cycloaddition Reactions in Organic Synthesis; Kobayashi, S.; Jorgensen, K. A., Eds.; Wiley-VCH: Weinheim, 2002, Chap. 6, 211.
20. (t) Kanemasa, S. In Cycloaddition Reactions in Organic Synthesis; Kobayashi, S.; Jorgensen, K. A., Eds.; Wiley-VCH: Weinheim, 2002, Chap. 7, 249.
21. (u) Kanemasa, S.; Nishiuchi, M.; Kamimura, A.; Hori, K. J. Am. Chem. Soc. 1994, 116, 2324.
22. (v) Singh, R.; Singh, S.; Bhella, A. K.; Sexana, M.; Faruk, A. S.; Ishar, M. P. S. Tetrahedron 2007, 63, 2283.
23. (w) Merino, P.; Tejero, T.; Laguna, M.; Cerrada, E.; Moreno, A.; Lopez, J. A. Org. Biomol. Chem. 2003, 1, 2336.
24. (x) Kumar, K. R. R.; Mallesha, H.; Rangappa, K. S. Synth. Commun. 2003, 33, 1545.
25. (y) Ding, X.; Taniguchi, K.; Ukaji, Y.; Inomata, K. Chem. Lett. 2001, 5, 468.
26. (z) Ooi, H.; Urushibara, A.; Esumi, T.; Iwabuchi, Y.; Hatakeyama, S. Org. Lett. 2001, 3, 953.
27. (aa) Romeo, G.; Iannazzoa, D.; Pipernoa, A.; Romeoa, R.; Corsarob, A.; Rescifinab, A.; Chiacchio, U. Mini-Rev. Org. Chem. 2005, 2, 59.
28. (a) Merino, P.; Franco, S.; Merchan, F. L.; Romero, P.; Tejero, T.; Uriel, S. Tetrahedron: Asymmetry 2003, 14, 3731.
29. (b) Torres-Sanchez, M. I.; Borrachero, P.; Cabrera-Escribano, F.; Gomez-Guillen, M.; Angulo-Alvarez, M.; Álvarez, E.; Favre, S.; Vogel, P. Tetrahedron: Asymmetry 2007, 18, 1809.
30. (a) Karanjule, N. S.; Markad, S. D.; Sharma, T.; Sabharwal, S. G.; Puranik, V. G.; Dhavale, D. D. J. Org. Chem. 2005, 70, 1356.
31. (b) Bande, O. P.; Jadhav, V. H.; Puranik, V. G.; Dhavale, D. D. Tetrahedron: Asymmetry 2007, 18, 1176.
32. (a) Elbein, A. D.; Molyneux, R. J. In Alkaloids: Chemical and Biological Perspectives, Vol. 5.; Pelletier, S. W., Ed.; Wiley-Interscience: New York, 1987.
33. (b) Howard, A. S.; Michael, J. P. In The Alkaloids, Vol. 28; Brossi, A., Ed.; Academic Press: New York, 1986, Chap. 3.
34. (c) Michael, J. P. Nat. Prod. Rep. 1990, 9, 485.
35. (a) Zho, H.; Hans, S.; Cheng, X.; Mootoo, D. R. J. Org. Chem. 2001, 66, 1761.
36. (b) Svansson, L.; Johnston, B. D.; Gu, J.-H.; Patrik, B.; Pinto, B. M. J. Am. Chem. Soc. 2000, 122. 10769.
37. (c) Izquiedro, I.; Plaza, M. T.; Robles, R.; Mota, A. J. Tetrahedron: Asymmetry 1998, 9, 1015.
38. (d) Kang, S. H.; Kim, J. S. Chem. Commun. 1998, 1353.
39. e) Kefalas, P.; Grierson, D. S. Tetrahedron Lett. 1993, 34, 3555.
40. (f) Ina, H.; Kibayashi, C. J. Org. Chem. 1993, 58, 52.
41. (g) Burgess, K.; Chaplin, D. A.; Henderson, I.; Pan, Y. T.; Elbein, A. D. J. Org. Chem. 1992, 57, 1103.
42. (h) Furneaux, R. H.; Mason, J. M.; Tyler, P. C. Tetrahedron Lett. 1995, 36, 3055.
43. (a) Truscheit, E.; Frommer, W.; Junge, B.; Muller, L.; Schmidt, D. D.; Wingender, W. Angew. Chem., Int. Ed. Engl. 1981, 20, 744.
44. (b) Furneaux, R. H.; Gainsford, G. J.; Mason, J. M.; Tyler, P. C.; Hartley, O.; Winchester, B. G. Tetrahedron 1997, 53, 245.
45. Humphries, M. J.; Matsumoto, K.; White, S. L.; Olden, K. Cancer Res. 1986, 46, 5215.
46. (a) Karpas, A.; Fleet, G. W. J.; Dwek, R. A.; Petursson, S.; Namgoong, S. K.; Ramsden, N. G.; Jacob, G. S.; Rademacher, T. W. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 9229.
47. (b) Walker, B. D.; Kowalski, M.; Goh, W. C.; Kozarsky, K.; Krieger, M.; Rosen, C.; Rohrschneider, L.; Haseltine, W. A.; Sodroski, J. Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 8120.
48. (c) Sunkara, P. S.; Bowling, T. L.; Liu, P. S.; Sjoerdsma, A. Biochem. Biophys. Res. Commun. 1987, 148, 206.
49. Johnson, H. A.; Thomas, N. R. Bioorg. Med. Chem. Lett. 2002, 12, 237.
50. (a) Kajimoto, T.; Liu, K. K. C.; Pederson, R. L.; Zhong, Z. Jr.; Ichikawa, Y.; Porco, J. A.; Wong, H. J. Am. Chem. Soc. 1991, 113, 6187.
51. (b) Asano, N.; Kato, A.; Miyauchi, M.; Kizu, H.; Kameda, Y.; Watson, A. A.; Nash, R. J.; Fleet, G. W. J. J. Nat. Prod. 1998, 61, 625.
52. (c) Bols, M.; Lillelund, V. H.; Jensen, H. H.; Liang, X. Chem. Rev. 2002, 102, 515; and references cited therein.
53. (d) Stutz, A. E. Iminosugars as Glycosidase Inhibitors, Nojirimycin and Beyond; Wiley-VCH: Weinheim, 1999.
54. (e) Heightman, T. D.; Vasella, A. T. Angew. Chem. Int. Ed. 1999, 38, 750.
55. (f) Jenson, H. H.; Bols, M. Acc. Chem. Res. 2006, 39, 259.
56. (g) Ichikawa, M.; Igarashi, Y.; Ichikawa, Y. Tetrahedron Lett. 1995, 36, 1767.
57. (h) Pandey, G.; Kapur, M.; Khan, M. I.; Gaikwad, S. M. Org. Biomol. Chem. 2003, 1, 3321.
58. (i) Matin, M. M.; Sharma, T.; Sabharwal, S. G.; Dhavale, D. D. Org. Biomol. Chem. 2005, 3, 1702.
59. Vyavahare, V. P.; Chakraborty, C.; Maity, B.; Chattopadhyay, S.; Puranik, V. G.; Dhavale, D. D. J. Med. Chem. 2007, 50, 5519.
60. (a) Markad, S. D.; Karanjule, N. S.; Sharma, T.; Sabharwal, S. G.; Puranik, V. G.; Dhavale, D. D. Org. Biomol. Chem. 2006, 4, 2549.
61. (b) Torres-Sanchez, M. I.; Borrachero, P.; Cabrera-Escribano, F.; Gomez-Guillen, M.; Angulo-Alvarez, M.; Dianez, M. J.; Estrada, M. D.; Lopez-Castro, A.; Perez-Garrido, S. Tetrahedron: Asymmetry 2005, 16, 3897.
62. (c) Lindsay, K. B.; Pyne, S. G. Tetrahedron 2004, 60, 4173.
63. (d) Tremmel, P.; Geyer, A. J. Am. Chem. Soc. 2002, 124, 8548.
64. (e) Gavard, O.; Hersant, Y.; Alais, J.; Duverger, V.; Dilhas, A.; Bascou, A.; Bonnaffe, D. Eur. J. Org. Chem. 2003, 3603.
65. (f) Geyer, A.; Bockelmann, D.; Weissenbach, K.; Fischer, H. Tetrahedron Lett. 1999, 40, 477.
66. (g) Nath, M.; Mukhopadhyay, R.; Bhattacharjya, A. Org. Lett. 2006, 8, 317.
67. (a) Karanjule, N. S.; Markad, S. D.; Dhavale, D. D. J. Org. Chem. 2006, 71, 6273.
68. (b) Dhavale, D. D.; Markad, S. D.; Karanjule, N. S.; PrakashaReddy, J. J. Org. Chem. 2004, 69, 4760.
69. (c) Patil, N. T.; Tilekar, J. N.; Dhavale, D. D. J. Org. Chem. 2001, 66, 1065; and references cited therein.
70. (a) Goti, A.; Cacciarini, M.; Cardona, F.; Brandi, A. Tetrahedron Lett. 1999, 40, 2853.
71. (b) Stafford, J. A. Tetrahedron Lett. 1995, 36, 681.
72. (c) Denmark, S. E.; Hurd, A. R. J. Org. Chem. 2000, 65, 2875.
73. (d) Denmark, S. E.; Seierstad, M.; Herbert, B. J. Org. Chem. 1999, 64, 884.
74. (e) Cicchi, S.; Marradi, M.; Vogel, P.; Goti, A. J. Org. Chem. 2006, 71, 1614.
75. (f) Closa, M.; Wightman, R. H. Synth. Commun. 1998, 28, 3443.
76. (g) Yu Y., Ohno M., Eguchi S., Kawai T., Terada Y.; Tetrahedron; 1997, 53: 5413.
77. (h) Argyropoulos, N. G.; Panagiotidis, T.; Coutouli-Argyropoulou, E.; Raptopoulou, C. Tetrahedron 2007, 63, 321.
78. Dondoni, A.; Franco, S.; Junquera, F.; Merchan, F.; Merino, P.; Tejero, T. Synth. Commun. 1994, 22, 2537.
79. 1H NMR spectrum of crude compound obtained from evaporation of toluene, showed additional signals (<7%) corresponding to unreacted dimethyl maleate. However, no other signals corresponding to other diastereomers were detected.
80. 7: C, 45.29; H, 7.22. Found: C, 49.31; H, 7.30.