Synthesis, and biological evaluation of conduritol, and conduramine analogs

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 5, 1999, Pages 621-628

  Desjardins, Michel ^a   Lallemand, Marie Christine ^a   Freeman, Stanley ^a   Hudlicky, Tomas ^a   Abboudf, Khalila ^a  

^a University of Florida ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0011702212     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a808329k     Document Type: Article

References (78)

1. M. Bald, Y. Sütbeyaz, and H. Seçen, Tetrahedron, 1990,46, 3715.
2. K. Kubier, Arch. Pharin., 1908, 246, 620.
3. G. Dangschat, and H. Fischer, Natunvissenschaflen, 1939, 27,756.
4. V. Plouvier, C. R. Seances Acad Sei., 1962,255, 360.
5. H. Kindl, and O. Hoflmann-Ostenhof, Forlsclir. Chan. Org. Naliirst., 1966,24, 149.
6. M. Nakajima, I. Tomida, and S. Takei, Chem. Ber., 1957,90,246.
7. (a) G. E. McCasland, and E. C. Horswill, J. Am. Chem. Soc., 1953,75,4020;
8. (b)T. L. Nagabhushan, Can. J. Chem., 1970,48,383; (c) H. Paulsen, W. Roben, and F. R. Heiker, Chem. Ber., 1981, 114, 3242;
9. R. A. Aleksejczyk, and G. A. Berchtold, J. Am. Chem. Soc., 1985,107, 2554;
10. (e) C. Le Drian, E. Vieira, and P. Vogel, Helv. Chim. Ada, 1989, 72, 338;
11. (f) H. Seçen, A. Maras, Y. Sütbeyaz, and M. Balci, Synlh. Commun., 1992, 22, 2613;
12. (g) T. Akiyama, H. Shima, M. Ohnari, T. Okazaki, and S. Osaki, Bull. Client. Soc. Jpn., 1993, 66, 3760.
13. (a) G. E. McCasland, and J. M. Reeves, J. Am. Client. Soc., 1955,77, 1812;
14. (b) C. R. Johnson, P. A. Ple, and J. P. Adams, J. Client. Soc., Chem. Commun., 1991, 1006;
15. H. Seçen, A. Maras, Y. Sütbeyaz, and M. Balci, Syntli. Commun., 1992, 22, 2613; (
16. (a) S. Angyal, and P. Gilham, J. Chem. Soc., 1955, 375;
17. (b) R. Criegee, and P. Becher, Client. Ber., 1957,90,2516.
18. (a) R. Angelaud, and Y. Landais, J. Org. Client., 1996, 61, 5202;
19. (b) S. J. Angyal, and P. T. Gilham, J. Chem. Soc., 1958, 375;
20. M. Nakajima, I. Tomida, and S. Takei, Client. Ber., 1957,90, 246.
21. (a) D. R. Boyd, and G. N. Sheldrake, Nat. Prod Rep, 1998, 15, 309;
22. (b) T. Hudlicky, Client. Rer., 1996, 96, 3;
23. T. Hudlicky, and A. J. Thorpc, Chem. Commun., 1996, 1993;
24. T. Hudlicky, in Green Chemistry: Designing Chemistry for the Environment, ed. P. T. Anastas, and T. C. Williamson, American Chemical Society, Washington, 1996, p. 180;
25. (e) T. Hudlicky, and J. W. Reed, in Advances in Asymmetric Synthesis, ed. A. Hassner, JAI Press, Greenwich, CT, 1995, Vol. 1, p. 271;
26. (f) A. D. Grund, SIM News 1995,45, 59;
27. (g) S. M. Brown, and T. Hudlicky, in Organic Synthesis: Theory, and Application, ed. T. Hudlicky, JAI Press, London, 1993, Vol. 2, p. 113;
28. (h) H. A. J. Carless, Tetrahedron: Asymmetry, 1992, 3, 795; (0 G. N. Sheldrake, in Chirality in Industry, ed. A. N Collins, G. N Sheldrake, and J. Crosby, Wiley, Chichester, 1992, p. 127; (_/') D. A. Widdowson, D. A. Ribbons, and S. D. Thomas, Jansscn Chim. Ada, 1990,8,3.
29. (a) L. E. Brammer, Jr., and T. Hudlicky, Tetrahedron: Asymmetry, 1998, 9, 2011;
30. (b) M. Desjardins, L. E. Brammer, Jr., and T. Hudlicky, Carbohydr. Res., 1997, 304, 39;
31. M. Mandel, and T. Hudlicky, J. Org. Client., 1993, 58, 2331; (
32. (e) H. A. J. Carless, and K. Busia, Carbohydr. Res., 1992, 234, 207;
33. (f) H. A. J. Carless, and S. S. Malik, Tetrahedron: Asymmetry, 1992, 3, 1135; (g)H. A. J. Carless, and O.Z. Oak, Tetrahedron Lett., 1991,32, 1671; (/i) H. A. J. Carless, and K. Busia, Tetrahedron Lett., 1990,31, 3449; (i) H. A. J. Carless, and K. Busia, Tetrahedron Lett., 1990, 31, 1617;
34. (j) H. A. J. Carless, J. R. Billinge, and O. Z. Oak, Tetrahedron Lett., 1989,30,3113.
35. (a) C. Sanfilippo, A. Patti, M. Piattelli, and G. Nicolosi, Tetrahedron: Asymmetry, 1997, 8, 1569;
36. (b) H. A. J. Carless, K. Busia, Y. Dove, and S. S. Malik, J. Chem. Soc., Perkin Trans, l, 1993, 2505;
37. H. A. J. Carless, Tetrahedron Lett., 1992, 33, 6379;
38. H. A. J. Carless, J. Chem. Soc., Client. Commun., 1992, 234;
39. (e) H. A. J. Carless, and O. Z. Oak, J. Chem. Soc., Chem. Commun., 1991,61;
40. (f) T. Hudlicky, H. Luna, H. F. Olivo, C., andersen, T. Nugent, and J. D. Price, J. Chem. Soc., Perkin Trans, l, 1991, 2907;
41. (g) T. Hudlicky, J. D. Price, and H. F. Olivo, Synlett, 1991, 645;
42. (h) T. Hudlicky, F. Rulin, T. Tsunoda, H. Luna, C., andersen, and J. D. Price, Isr. J. Chem., 1991,31, 229; (<) S. V. Ley, and A. J. Redgrave, Synlett, 1990, 393;
43. H. A. J. Carless, and O. Z. Oak, Tetrahedron Lett., 1989, 30, 1719.
44. (a) K. R. Shanmugasundaram, C. Panneerselvan, P. Samudram, and E. R. B. Shanmugasundaram, J. Ethnopharmacot., 1983, 7, 205.
45. (b) K. R. Shanmugasundaram, C. Panneerselvan, P. Samudram, and E. R. B. Shanmugasundaram, Pharmacol. Res. Commun., 1981,13, 475.
46. C. Day, in New Antidiabetic Drugs, ed. C. J. Bailey, and P. R. Flatt, Smith-Gordon, London, 1990, p. 267.
47. K. Miyatake, S. Takenaka, T. Fujimoto, G. Kensho, S. P. Upadhaya, M. Kirihata, I. Ichimoto, and Y. Nakano, Biosci. Biotechnol. Biochem., 1993,57,2184.
48. (a) S. Atsumi, K. Umezawa, H. linuma, H. Naganawa, H. Nakamura, Y. litaka, and J. Antibiot., 1990, 43, 49;
49. (b) G. Legier, in Methods in Enzymology, ed. W. B. Jakoby, and M. Wilchek, Academic Press, New York, 1977, vol. XLVI, p. 368-381;
50. G. Legier, and E. Bause, Carbohydr. Res., 1973, 28, 45;
51. G. Legier, Mol. Cell. Biochem., 1973, 2, 31;
52. K. T. Cavanagh, R. A. Fisher, G. Legier, M. Herrchen, M. Z. Jones, E. Julien, R. P. Sewell-Alger, M. L. Sinnott, and F. E. Wilkinson, Enzyme, 1985, 34, 75;
53. G. Legier, and W. Lotz, Hoppe-Seyler's Z. Physiol. Chem., 1973,354, 243.
54. (a) M. Balci, Pure Appl. Chem., 1997, 69, 97;
55. (b) T. Hudlicky, and M. Cebulak, Cyclitols, and their Derivatives, VCH, 1993.
56. D. C. Billington, F. Perron-Sierra, I. Picard, S. Beaubras, J. Duhault, J. Espinal, and S. Challal, Bioorg. Med. Chem. Lett., 1994,4,2307.
57. Y. Kara, M. Balci, S. A. Bourne, and W. H. Watson, Tetrahedron Lett., 1994,35, 3349.
58. (a) M. Desjardins, M. C. Lallemand, T. Hudlicky, and K. A. Abboud, Synlelt, 1997, 728;
59. (b) M. C. Lallemand, M. Desjardins, S. Freeman, and T. Hudlicky, Tetrahedron Lett., 1997, 38, 7693.
60. (a) A. M. Jeffrey, H. J. Yeh, D. M. Jerina, T. R. Patel, J. F. Davey, and D. T. Gibson, Biochemistry, 1975, 14, 575;
61. (b) F. A. Catterall, K. Murray, and P. A. Williams, Biochem. Biophys. Acta, 1971, 237, 361;
62. C. E. Cerniglia, D. T. Gibson, and C. van Baalen, J. Gcn. Microbiol., 1980, 116, 495;
63. C. E. Cerniglia, C. van Baalen, and D. T. Gibson, J. Gen. Microbioi., 1980,116,485;
64. (e) C. E. Cerniglia, D. T. Gibson, and C. van Baalen, Biochem. Biophys. Res. Commun., 1979,88,50;
65. (f) M. A. Heitkamp, J. P. Freeman, and C. E. Cerniglia, App. Environ. Microbioi., 1987,53, 129.
66. G. J. Zylstra, and D. T. Gibson, J. Biol. Client., 1989, 264, 14940.
67. F. Orsini, and F. Pelizzoni, Tetrahedron: Asymmetry, 1996, 7, 1033.
68. (a) T. Hudlicky, K. A. Abboud, J. Bolonick, R. Maurya, M. L. Stanton, and A. J. Thorpe, Client. Commun. 1996, 1717;
69. (b) T. Hudlicky, and A. J. Thorpe, Synlelt, 1994, 899;
70. T. Hudlicky, K. A. Abboud, D. A/Entwistle, R. Fan, R. Maurya, A. J. Thorpe, J. Bolonick, and B. Myers, Synthesis, 1996, 897.
71. Z. Li, R. W. Quan, and E. N. Jacobsen, J. Am. Cliem. Soc., 1995,117, 5889.
72. D. A. Evans, M. M. Faul, and M. T. Bilodeau, J. Org. Client., 1991, 56, 6744.
73. Improved yields for this reaction were obtained using a modified nitrene precursor, see: M. J. Sodergren, D. A. Alonso, A. V. Bedekar, and P. G., anderson, Tetrahedron Lett., 1997,38, 6897.
74. C. M. G. Löfström, A. M. Ericsson, L. Bourrinet, S. K. Juntunen, and J. E. Backvall, J. Org. Client., 1995,60, 3586.
75. (a) K. Sugahara, and I. Yamashina, in Methods in En:ymohgy, ed. V. Ginsburg, Academic Press, New York, 1972, vol. XXVIII, Part B, pp. 769-772;
76. (b) A. L. Tarentino, and F. Maley, in Methods in Eniyntology, ed. V. Ginsburg, Academic Press, New York, 1972, vol. XXVIII, Part B, pp. 772-776;
77. F. Petek, E. Villarroya, and J. E. Courtois, Eur. J. Biochem., 1969, 8, 395;
78. G. R. Craven, E. Jr. Steers, and C. B. Anfinsen, J. Biol. Client., 1965, 240,2468.