Aza-C-disaccharides: Synthesis of 6-deoxygalactonojirimycin β-C(1→3) linked with D-altrofuranosides and D-galactose

Journal of Organic Chemistry

Volumn 62, Issue 18, 1997, Pages 6252-6260

  Baudat, Alain ^a   Vogel, Pierre ^a  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

6 DEOXYGALACTONOJIRIMYCIN BETA D ALTROFURANOSIDE; 6 DEOXYGALACTONOJIRIMYCIN BETA D GALACTOSE; DISACCHARIDE; FURAN DERIVATIVE; GALACTOSE; UNCLASSIFIED DRUG;

ARTICLE; BACTERIAL INFECTION; CATALYSIS; DRUG CONFORMATION; DRUG SYNTHESIS; ENZYME INHIBITION; HYDROLYSIS; NONHUMAN; SUGAR TRANSPORT; VIRUS CELL INTERACTION;

EID: 0030761398     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970151t     Document Type: Article

References (75)

1. See, e.g.: Rademacher, T. W.; Parekh, R. B.; Dwek, R. A. Annu. Rev. Biochem. 1988, 57, 785. Hindsgaul, O.; Khare, D. P.; Bach, M.; Lemieux, R. U. Can. J. Chem. 1985, 63, 2653. Feizi, T. In Carbohydrate Recognition in Cellular Function; Ciba Geigy Symposium 145; Wiley: Chichester, 1989; pp 62-79. Kornfeld, R.; Kornfeld, S. Annu. Rev. Biochem. 1985, 54, 631. Moremen, K. W.; Trimble, R. B.; Herscovics, A. Glycobiology 1994, 4, 113. Rice, G. E.; Bevilacqua, M. P. Science 1989, 246, 1303. Smith, C. A.; Davis, T.; Anderson, D.; Solam, L.; Beckmann, M. P.; Jerzy, R.; Dower, S. K.; Cosman, D.; Goodwin, R. G. Science 1990, 248, 1019.
2. See, e.g.: Rademacher, T. W.; Parekh, R. B.; Dwek, R. A. Annu. Rev. Biochem. 1988, 57, 785. Hindsgaul, O.; Khare, D. P.; Bach, M.; Lemieux, R. U. Can. J. Chem. 1985, 63, 2653. Feizi, T. In Carbohydrate Recognition in Cellular Function; Ciba Geigy Symposium 145; Wiley: Chichester, 1989; pp 62-79. Kornfeld, R.; Kornfeld, S. Annu. Rev. Biochem. 1985, 54, 631. Moremen, K. W.; Trimble, R. B.; Herscovics, A. Glycobiology 1994, 4, 113. Rice, G. E.; Bevilacqua, M. P. Science 1989, 246, 1303. Smith, C. A.; Davis, T.; Anderson, D.; Solam, L.; Beckmann, M. P.; Jerzy, R.; Dower, S. K.; Cosman, D.; Goodwin, R. G. Science 1990, 248, 1019.
3. See, e.g.: Rademacher, T. W.; Parekh, R. B.; Dwek, R. A. Annu. Rev. Biochem. 1988, 57, 785. Hindsgaul, O.; Khare, D. P.; Bach, M.; Lemieux, R. U. Can. J. Chem. 1985, 63, 2653. Feizi, T. In Carbohydrate Recognition in Cellular Function; Ciba Geigy Symposium 145; Wiley: Chichester, 1989; pp 62-79. Kornfeld, R.; Kornfeld, S. Annu. Rev. Biochem. 1985, 54, 631. Moremen, K. W.; Trimble, R. B.; Herscovics, A. Glycobiology 1994, 4, 113. Rice, G. E.; Bevilacqua, M. P. Science 1989, 246, 1303. Smith, C. A.; Davis, T.; Anderson, D.; Solam, L.; Beckmann, M. P.; Jerzy, R.; Dower, S. K.; Cosman, D.; Goodwin, R. G. Science 1990, 248, 1019.
4. See, e.g.: Rademacher, T. W.; Parekh, R. B.; Dwek, R. A. Annu. Rev. Biochem. 1988, 57, 785. Hindsgaul, O.; Khare, D. P.; Bach, M.; Lemieux, R. U. Can. J. Chem. 1985, 63, 2653. Feizi, T. In Carbohydrate Recognition in Cellular Function; Ciba Geigy Symposium 145; Wiley: Chichester, 1989; pp 62-79. Kornfeld, R.; Kornfeld, S. Annu. Rev. Biochem. 1985, 54, 631. Moremen, K. W.; Trimble, R. B.; Herscovics, A. Glycobiology 1994, 4, 113. Rice, G. E.; Bevilacqua, M. P. Science 1989, 246, 1303. Smith, C. A.; Davis, T.; Anderson, D.; Solam, L.; Beckmann, M. P.; Jerzy, R.; Dower, S. K.; Cosman, D.; Goodwin, R. G. Science 1990, 248, 1019.
5. See, e.g.: Rademacher, T. W.; Parekh, R. B.; Dwek, R. A. Annu. Rev. Biochem. 1988, 57, 785. Hindsgaul, O.; Khare, D. P.; Bach, M.; Lemieux, R. U. Can. J. Chem. 1985, 63, 2653. Feizi, T. In Carbohydrate Recognition in Cellular Function; Ciba Geigy Symposium 145; Wiley: Chichester, 1989; pp 62-79. Kornfeld, R.; Kornfeld, S. Annu. Rev. Biochem. 1985, 54, 631. Moremen, K. W.; Trimble, R. B.; Herscovics, A. Glycobiology 1994, 4, 113. Rice, G. E.; Bevilacqua, M. P. Science 1989, 246, 1303. Smith, C. A.; Davis, T.; Anderson, D.; Solam, L.; Beckmann, M. P.; Jerzy, R.; Dower, S. K.; Cosman, D.; Goodwin, R. G. Science 1990, 248, 1019.
6. See, e.g.: Rademacher, T. W.; Parekh, R. B.; Dwek, R. A. Annu. Rev. Biochem. 1988, 57, 785. Hindsgaul, O.; Khare, D. P.; Bach, M.; Lemieux, R. U. Can. J. Chem. 1985, 63, 2653. Feizi, T. In Carbohydrate Recognition in Cellular Function; Ciba Geigy Symposium 145; Wiley: Chichester, 1989; pp 62-79. Kornfeld, R.; Kornfeld, S. Annu. Rev. Biochem. 1985, 54, 631. Moremen, K. W.; Trimble, R. B.; Herscovics, A. Glycobiology 1994, 4, 113. Rice, G. E.; Bevilacqua, M. P. Science 1989, 246, 1303. Smith, C. A.; Davis, T.; Anderson, D.; Solam, L.; Beckmann, M. P.; Jerzy, R.; Dower, S. K.; Cosman, D.; Goodwin, R. G. Science 1990, 248, 1019.
7. See, e.g.: Rademacher, T. W.; Parekh, R. B.; Dwek, R. A. Annu. Rev. Biochem. 1988, 57, 785. Hindsgaul, O.; Khare, D. P.; Bach, M.; Lemieux, R. U. Can. J. Chem. 1985, 63, 2653. Feizi, T. In Carbohydrate Recognition in Cellular Function; Ciba Geigy Symposium 145; Wiley: Chichester, 1989; pp 62-79. Kornfeld, R.; Kornfeld, S. Annu. Rev. Biochem. 1985, 54, 631. Moremen, K. W.; Trimble, R. B.; Herscovics, A. Glycobiology 1994, 4, 113. Rice, G. E.; Bevilacqua, M. P. Science 1989, 246, 1303. Smith, C. A.; Davis, T.; Anderson, D.; Solam, L.; Beckmann, M. P.; Jerzy, R.; Dower, S. K.; Cosman, D.; Goodwin, R. G. Science 1990, 248, 1019.
8. See, e.g.: Sinnott, M. L. Chem. Rev. 1990, 90, 1171. Legler, G. Adv. Carbohydr. Chem. Biochem. 1990, 48, 319. Franck, R. W. Bioorg. Chem. 1992, 20, 77. Kirby, A. J. Adv. Phys. Org. Chem. 1994, 5, 605.
9. See, e.g.: Sinnott, M. L. Chem. Rev. 1990, 90, 1171. Legler, G. Adv. Carbohydr. Chem. Biochem. 1990, 48, 319. Franck, R. W. Bioorg. Chem. 1992, 20, 77. Kirby, A. J. Adv. Phys. Org. Chem. 1994, 5, 605.
10. See, e.g.: Sinnott, M. L. Chem. Rev. 1990, 90, 1171. Legler, G. Adv. Carbohydr. Chem. Biochem. 1990, 48, 319. Franck, R. W. Bioorg. Chem. 1992, 20, 77. Kirby, A. J. Adv. Phys. Org. Chem. 1994, 5, 605.
11. See, e.g.: Sinnott, M. L. Chem. Rev. 1990, 90, 1171. Legler, G. Adv. Carbohydr. Chem. Biochem. 1990, 48, 319. Franck, R. W. Bioorg. Chem. 1992, 20, 77. Kirby, A. J. Adv. Phys. Org. Chem. 1994, 5, 605.
12. See e.g.: Winchester, B.; Fleet, G. W. J. Glycobiol. 1992, 2, 199. Karlsson, G. B.; Butters, T. D.; Dwek, R. A.; Platt, R. M. J. Biol. Chem. 1993, 268, 570. Colman, P. M. Pure Appl. Chem. 1995, 67, 1683.
13. See e.g.: Winchester, B.; Fleet, G. W. J. Glycobiol. 1992, 2, 199. Karlsson, G. B.; Butters, T. D.; Dwek, R. A.; Platt, R. M. J. Biol. Chem. 1993, 268, 570. Colman, P. M. Pure Appl. Chem. 1995, 67, 1683.
14. See e.g.: Winchester, B.; Fleet, G. W. J. Glycobiol. 1992, 2, 199. Karlsson, G. B.; Butters, T. D.; Dwek, R. A.; Platt, R. M. J. Biol. Chem. 1993, 268, 570. Colman, P. M. Pure Appl. Chem. 1995, 67, 1683.
15. See, e.g.: Look, G. C.; Fotsch, C. H.; Wong, C.-H. Acc. Chem. Res. 1993, 26, 182. Wong, C.-H.; Provencher, L.; Porco, J. A.; Jung, S.-H.; Wang, Y.-F.; Chen, L.; Wang, R.; Steensma, D. H. J. Org. Chem. 1995, 60, 1492. Wang, Y.-F.; Takaoka, Y., Wong, C.-H. Angew. Chem., Int. Ed. Engl. 1994, 35, 1242. Asano, N.; Oseki, K.; Kizu, H., Matsui, K. J. Med. Chem. 1994, 37, 3701. McCarter, J. D.; Withers, S. G. Curr. Opin. Struct. Biol. 1994, 4, 885. Papandreou, G.; Tong, M. K.; Ganem, B. J. Am. Chem. Soc. 1993, 115, 11682. Moris-Varas, F.; Qian, X.-H.; Wong, C.-H. Ibid. 1996, 118, 7647. Ganem, B. Acc. Chem. Res. 1996, 29, 340. Wong, C.-H.; Halcomb, R. L.; Ichikawa, Y., Kajimoto, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 521.
16. See, e.g.: Look, G. C.; Fotsch, C. H.; Wong, C.-H. Acc. Chem. Res. 1993, 26, 182. Wong, C.-H.; Provencher, L.; Porco, J. A.; Jung, S.-H.; Wang, Y.-F.; Chen, L.; Wang, R.; Steensma, D. H. J. Org. Chem. 1995, 60, 1492. Wang, Y.-F.; Takaoka, Y., Wong, C.-H. Angew. Chem., Int. Ed. Engl. 1994, 35, 1242. Asano, N.; Oseki, K.; Kizu, H., Matsui, K. J. Med. Chem. 1994, 37, 3701. McCarter, J. D.; Withers, S. G. Curr. Opin. Struct. Biol. 1994, 4, 885. Papandreou, G.; Tong, M. K.; Ganem, B. J. Am. Chem. Soc. 1993, 115, 11682. Moris-Varas, F.; Qian, X.-H.; Wong, C.-H. Ibid. 1996, 118, 7647. Ganem, B. Acc. Chem. Res. 1996, 29, 340. Wong, C.-H.; Halcomb, R. L.; Ichikawa, Y., Kajimoto, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 521.
17. See, e.g.: Look, G. C.; Fotsch, C. H.; Wong, C.-H. Acc. Chem. Res. 1993, 26, 182. Wong, C.-H.; Provencher, L.; Porco, J. A.; Jung, S.-H.; Wang, Y.-F.; Chen, L.; Wang, R.; Steensma, D. H. J. Org. Chem. 1995, 60, 1492. Wang, Y.-F.; Takaoka, Y., Wong, C.-H. Angew. Chem., Int. Ed. Engl. 1994, 35, 1242. Asano, N.; Oseki, K.; Kizu, H., Matsui, K. J. Med. Chem. 1994, 37, 3701. McCarter, J. D.; Withers, S. G. Curr. Opin. Struct. Biol. 1994, 4, 885. Papandreou, G.; Tong, M. K.; Ganem, B. J. Am. Chem. Soc. 1993, 115, 11682. Moris-Varas, F.; Qian, X.-H.; Wong, C.-H. Ibid. 1996, 118, 7647. Ganem, B. Acc. Chem. Res. 1996, 29, 340. Wong, C.-H.; Halcomb, R. L.; Ichikawa, Y., Kajimoto, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 521.
18. See, e.g.: Look, G. C.; Fotsch, C. H.; Wong, C.-H. Acc. Chem. Res. 1993, 26, 182. Wong, C.-H.; Provencher, L.; Porco, J. A.; Jung, S.-H.; Wang, Y.-F.; Chen, L.; Wang, R.; Steensma, D. H. J. Org. Chem. 1995, 60, 1492. Wang, Y.-F.; Takaoka, Y., Wong, C.-H. Angew. Chem., Int. Ed. Engl. 1994, 35, 1242. Asano, N.; Oseki, K.; Kizu, H., Matsui, K. J. Med. Chem. 1994, 37, 3701. McCarter, J. D.; Withers, S. G. Curr. Opin. Struct. Biol. 1994, 4, 885. Papandreou, G.; Tong, M. K.; Ganem, B. J. Am. Chem. Soc. 1993, 115, 11682. Moris-Varas, F.; Qian, X.-H.; Wong, C.-H. Ibid. 1996, 118, 7647. Ganem, B. Acc. Chem. Res. 1996, 29, 340. Wong, C.-H.; Halcomb, R. L.; Ichikawa, Y., Kajimoto, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 521.
19. See, e.g.: Look, G. C.; Fotsch, C. H.; Wong, C.-H. Acc. Chem. Res. 1993, 26, 182. Wong, C.-H.; Provencher, L.; Porco, J. A.; Jung, S.-H.; Wang, Y.-F.; Chen, L.; Wang, R.; Steensma, D. H. J. Org. Chem. 1995, 60, 1492. Wang, Y.-F.; Takaoka, Y., Wong, C.-H. Angew. Chem., Int. Ed. Engl. 1994, 35, 1242. Asano, N.; Oseki, K.; Kizu, H., Matsui, K. J. Med. Chem. 1994, 37, 3701. McCarter, J. D.; Withers, S. G. Curr. Opin. Struct. Biol. 1994, 4, 885. Papandreou, G.; Tong, M. K.; Ganem, B. J. Am. Chem. Soc. 1993, 115, 11682. Moris-Varas, F.; Qian, X.-H.; Wong, C.-H. Ibid. 1996, 118, 7647. Ganem, B. Acc. Chem. Res. 1996, 29, 340. Wong, C.-H.; Halcomb, R. L.; Ichikawa, Y., Kajimoto, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 521.
20. See, e.g.: Look, G. C.; Fotsch, C. H.; Wong, C.-H. Acc. Chem. Res. 1993, 26, 182. Wong, C.-H.; Provencher, L.; Porco, J. A.; Jung, S.-H.; Wang, Y.-F.; Chen, L.; Wang, R.; Steensma, D. H. J. Org. Chem. 1995, 60, 1492. Wang, Y.-F.; Takaoka, Y., Wong, C.-H. Angew. Chem., Int. Ed. Engl. 1994, 35, 1242. Asano, N.; Oseki, K.; Kizu, H., Matsui, K. J. Med. Chem. 1994, 37, 3701. McCarter, J. D.; Withers, S. G. Curr. Opin. Struct. Biol. 1994, 4, 885. Papandreou, G.; Tong, M. K.; Ganem, B. J. Am. Chem. Soc. 1993, 115, 11682. Moris-Varas, F.; Qian, X.-H.; Wong, C.-H. Ibid. 1996, 118, 7647. Ganem, B. Acc. Chem. Res. 1996, 29, 340. Wong, C.-H.; Halcomb, R. L.; Ichikawa, Y., Kajimoto, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 521.
21. See, e.g.: Look, G. C.; Fotsch, C. H.; Wong, C.-H. Acc. Chem. Res. 1993, 26, 182. Wong, C.-H.; Provencher, L.; Porco, J. A.; Jung, S.-H.; Wang, Y.-F.; Chen, L.; Wang, R.; Steensma, D. H. J. Org. Chem. 1995, 60, 1492. Wang, Y.-F.; Takaoka, Y., Wong, C.-H. Angew. Chem., Int. Ed. Engl. 1994, 35, 1242. Asano, N.; Oseki, K.; Kizu, H., Matsui, K. J. Med. Chem. 1994, 37, 3701. McCarter, J. D.; Withers, S. G. Curr. Opin. Struct. Biol. 1994, 4, 885. Papandreou, G.; Tong, M. K.; Ganem, B. J. Am. Chem. Soc. 1993, 115, 11682. Moris-Varas, F.; Qian, X.-H.; Wong, C.-H. Ibid. 1996, 118, 7647. Ganem, B. Acc. Chem. Res. 1996, 29, 340. Wong, C.-H.; Halcomb, R. L.; Ichikawa, Y., Kajimoto, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 521.
22. See, e.g.: Look, G. C.; Fotsch, C. H.; Wong, C.-H. Acc. Chem. Res. 1993, 26, 182. Wong, C.-H.; Provencher, L.; Porco, J. A.; Jung, S.-H.; Wang, Y.-F.; Chen, L.; Wang, R.; Steensma, D. H. J. Org. Chem. 1995, 60, 1492. Wang, Y.-F.; Takaoka, Y., Wong, C.-H. Angew. Chem., Int. Ed. Engl. 1994, 35, 1242. Asano, N.; Oseki, K.; Kizu, H., Matsui, K. J. Med. Chem. 1994, 37, 3701. McCarter, J. D.; Withers, S. G. Curr. Opin. Struct. Biol. 1994, 4, 885. Papandreou, G.; Tong, M. K.; Ganem, B. J. Am. Chem. Soc. 1993, 115, 11682. Moris-Varas, F.; Qian, X.-H.; Wong, C.-H. Ibid. 1996, 118, 7647. Ganem, B. Acc. Chem. Res. 1996, 29, 340. Wong, C.-H.; Halcomb, R. L.; Ichikawa, Y., Kajimoto, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 521.
23. See, e.g.: Look, G. C.; Fotsch, C. H.; Wong, C.-H. Acc. Chem. Res. 1993, 26, 182. Wong, C.-H.; Provencher, L.; Porco, J. A.; Jung, S.-H.; Wang, Y.-F.; Chen, L.; Wang, R.; Steensma, D. H. J. Org. Chem. 1995, 60, 1492. Wang, Y.-F.; Takaoka, Y., Wong, C.-H. Angew. Chem., Int. Ed. Engl. 1994, 35, 1242. Asano, N.; Oseki, K.; Kizu, H., Matsui, K. J. Med. Chem. 1994, 37, 3701. McCarter, J. D.; Withers, S. G. Curr. Opin. Struct. Biol. 1994, 4, 885. Papandreou, G.; Tong, M. K.; Ganem, B. J. Am. Chem. Soc. 1993, 115, 11682. Moris-Varas, F.; Qian, X.-H.; Wong, C.-H. Ibid. 1996, 118, 7647. Ganem, B. Acc. Chem. Res. 1996, 29, 340. Wong, C.-H.; Halcomb, R. L.; Ichikawa, Y., Kajimoto, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 521.
24. See, e.g.: Rye, P. D.; Bovin, N. V.; Vlasova, E. V.; Walker, R. A. Glycobiology 1995, 5, 385.
25. Johnson, C. R.; Miller, M. W.; Golebiowski, A.; Sundram, H.; Ksebati, M. B. Tetrahedron Lett. 1994, 35, 8991.
26. Martin, O. R.; Liu, L.; Yang, F. Tetrahedron Lett. 1996, 37, 1991.
27. Baudat, A.; Vogel, P. Tetrahedron Lett. 1996, 37, 483.
28. Frérot, E.; Marquis, C.; Vogel, P. Tetrahedron Lett. 1996, 37, 2023.
29. An azapyranosyl disaccharide with a thioglycosidic linkage has been described: Suzuki, K.; Hashimoto, H. Tetrahedron Lett. 1994, 35, 4119.
30. β-L-Xylopyranosides (1→6) of 2,5-dideoxy-2,5-iminoaltitols have been prepared: Mikkelsen, G.; Christensen, T. V.; Bols, M.; Lundt, I.; Sierks, M. R. Tetrahedron Lett. 1995, 36, 6541. See also: Andrews, J. S.; Weimar, T.; Frandsen, T. P.; Svensson, B.; Pinto, B. M. J. Am. Chem. Soc. 1995, 117, 10799.
31. β-L-Xylopyranosides (1→6) of 2,5-dideoxy-2,5-iminoaltitols have been prepared: Mikkelsen, G.; Christensen, T. V.; Bols, M.; Lundt, I.; Sierks, M. R. Tetrahedron Lett. 1995, 36, 6541. See also: Andrews, J. S.; Weimar, T.; Frandsen, T. P.; Svensson, B.; Pinto, B. M. J. Am. Chem. Soc. 1995, 117, 10799.
32. See, e.g.; MacLean, G. D.; Longenecker, B. M. Can. J. Oncol. 1994, 4, 249.
33. Brimacombe, J. S.; Tucker, L. C. N. Carbohydr. Res. 1966, 2, 341.
34. Shing, T. K. M.; Zhou, Z.-H.; Tsui, H.-C.; Mak, T. C. W. J. Chem. Soc., Perkin Trans. I 1992, 887.
35. Baudat, A.; Picasso, S.; Vogel, P. Carbohydr. Res. 1996, 281, 277.
36. (a) Black, K. A.; Vogel, P. J. Org. Chem. 1986, 51, 5341.
37. (b) Gasparini, F.; Vogel, P. Ibid. 1990, 55, 2451.
38. (c) Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173.
39. (d) Reymond, J.-L.; Vogel, P. Tetrahedron: Asymmetry 1990, 1, 729.
40. For alternative methods of preparations of enantiomerically pure 7-oxabicyclo[2.2.1]hept-5-en-ones precursors of (+)-13 and (-)-13, see: Saf, R.; Faber, K.; Penn, G.; Griengl, H. Tetrahedron 1988, 44, 389. Ronan, B.; Kagan, H. B. Tetrahedron: Asymmetry 1991, 2, 75. Corey, E. J.; Loh, T.-P. Tetrahedron Lett. 1993, 34, 3979.
41. For alternative methods of preparations of enantiomerically pure 7-oxabicyclo[2.2.1]hept-5-en-ones precursors of (+)-13 and (-)-13, see: Saf, R.; Faber, K.; Penn, G.; Griengl, H. Tetrahedron 1988, 44, 389. Ronan, B.; Kagan, H. B. Tetrahedron: Asymmetry 1991, 2, 75. Corey, E. J.; Loh, T.-P. Tetrahedron Lett. 1993, 34, 3979.
42. For alternative methods of preparations of enantiomerically pure 7-oxabicyclo[2.2.1]hept-5-en-ones precursors of (+)-13 and (-)-13, see: Saf, R.; Faber, K.; Penn, G.; Griengl, H. Tetrahedron 1988, 44, 389. Ronan, B.; Kagan, H. B. Tetrahedron: Asymmetry 1991, 2, 75. Corey, E. J.; Loh, T.-P. Tetrahedron Lett. 1993, 34, 3979.
43. Gagnaire, D.; Payo-Subiza, E. Bull. Soc. Chim. Fr. 1963, 2627. Ramey, K. C.; Lini, D. C. J. Magn. Reson. 1970, 3, 94. Nelson, W. L.; Allen, D. R. J. Heterocycl. Chem. 1972, 9, 561. Kienzle, F. Helv. Chim. Acta 1975, 50, 1180. Mahaim, C.; Vogel, P. Ibid. 1982, 65, 866.
44. Gagnaire, D.; Payo-Subiza, E. Bull. Soc. Chim. Fr. 1963, 2627. Ramey, K. C.; Lini, D. C. J. Magn. Reson. 1970, 3, 94. Nelson, W. L.; Allen, D. R. J. Heterocycl. Chem. 1972, 9, 561. Kienzle, F. Helv. Chim. Acta 1975, 50, 1180. Mahaim, C.; Vogel, P. Ibid. 1982, 65, 866.
45. Gagnaire, D.; Payo-Subiza, E. Bull. Soc. Chim. Fr. 1963, 2627. Ramey, K. C.; Lini, D. C. J. Magn. Reson. 1970, 3, 94. Nelson, W. L.; Allen, D. R. J. Heterocycl. Chem. 1972, 9, 561. Kienzle, F. Helv. Chim. Acta 1975, 50, 1180. Mahaim, C.; Vogel, P. Ibid. 1982, 65, 866.
46. Gagnaire, D.; Payo-Subiza, E. Bull. Soc. Chim. Fr. 1963, 2627. Ramey, K. C.; Lini, D. C. J. Magn. Reson. 1970, 3, 94. Nelson, W. L.; Allen, D. R. J. Heterocycl. Chem. 1972, 9, 561. Kienzle, F. Helv. Chim. Acta 1975, 50, 1180. Mahaim, C.; Vogel, P. Ibid. 1982, 65, 866.
47. Gagnaire, D.; Payo-Subiza, E. Bull. Soc. Chim. Fr. 1963, 2627. Ramey, K. C.; Lini, D. C. J. Magn. Reson. 1970, 3, 94. Nelson, W. L.; Allen, D. R. J. Heterocycl. Chem. 1972, 9, 561. Kienzle, F. Helv. Chim. Acta 1975, 50, 1180. Mahaim, C.; Vogel, P. Ibid. 1982, 65, 866.
48. Zimmerman, H. E.; Traxler, M. D. J. Am. Chem. Soc. 1957, 79, 1920. See also: Kleschick, W. A.; Buse, C. T.; Heathcock, C. H. Ibid. 1977, 99, 247. Fellmann, P.; Dubois, J. E. Tetrahedron 1978, 34, 1349. Evans, D. A.; Vogel, E.; Nelson, J. V. J. Am. Chem. Soc. 1979, 101, 6120. Heathcock, C. H.; Buse, C. T.; Kleschick, W. A.; Pirrung, M. C.; Sohn, J. E.; Lampe, J. J. Org. Chem. 1980, 45, 1066. Anh, N. T.; Elkaïm, L.; Thanh, B. T.; Maurel, F.; Flament, J. P. Bull. Soc. Chim. Fr. 1992, 129, 468.
49. Zimmerman, H. E.; Traxler, M. D. J. Am. Chem. Soc. 1957, 79, 1920. See also: Kleschick, W. A.; Buse, C. T.; Heathcock, C. H. Ibid. 1977, 99, 247. Fellmann, P.; Dubois, J. E. Tetrahedron 1978, 34, 1349. Evans, D. A.; Vogel, E.; Nelson, J. V. J. Am. Chem. Soc. 1979, 101, 6120. Heathcock, C. H.; Buse, C. T.; Kleschick, W. A.; Pirrung, M. C.; Sohn, J. E.; Lampe, J. J. Org. Chem. 1980, 45, 1066. Anh, N. T.; Elkaïm, L.; Thanh, B. T.; Maurel, F.; Flament, J. P. Bull. Soc. Chim. Fr. 1992, 129, 468.
50. Zimmerman, H. E.; Traxler, M. D. J. Am. Chem. Soc. 1957, 79, 1920. See also: Kleschick, W. A.; Buse, C. T.; Heathcock, C. H. Ibid. 1977, 99, 247. Fellmann, P.; Dubois, J. E. Tetrahedron 1978, 34, 1349. Evans, D. A.; Vogel, E.; Nelson, J. V. J. Am. Chem. Soc. 1979, 101, 6120. Heathcock, C. H.; Buse, C. T.; Kleschick, W. A.; Pirrung, M. C.; Sohn, J. E.; Lampe, J. J. Org. Chem. 1980, 45, 1066. Anh, N. T.; Elkaïm, L.; Thanh, B. T.; Maurel, F.; Flament, J. P. Bull. Soc. Chim. Fr. 1992, 129, 468.
51. Zimmerman, H. E.; Traxler, M. D. J. Am. Chem. Soc. 1957, 79, 1920. See also: Kleschick, W. A.; Buse, C. T.; Heathcock, C. H. Ibid. 1977, 99, 247. Fellmann, P.; Dubois, J. E. Tetrahedron 1978, 34, 1349. Evans, D. A.; Vogel, E.; Nelson, J. V. J. Am. Chem. Soc. 1979, 101, 6120. Heathcock, C. H.; Buse, C. T.; Kleschick, W. A.; Pirrung, M. C.; Sohn, J. E.; Lampe, J. J. Org. Chem. 1980, 45, 1066. Anh, N. T.; Elkaïm, L.; Thanh, B. T.; Maurel, F.; Flament, J. P. Bull. Soc. Chim. Fr. 1992, 129, 468.
52. Zimmerman, H. E.; Traxler, M. D. J. Am. Chem. Soc. 1957, 79, 1920. See also: Kleschick, W. A.; Buse, C. T.; Heathcock, C. H. Ibid. 1977, 99, 247. Fellmann, P.; Dubois, J. E. Tetrahedron 1978, 34, 1349. Evans, D. A.; Vogel, E.; Nelson, J. V. J. Am. Chem. Soc. 1979, 101, 6120. Heathcock, C. H.; Buse, C. T.; Kleschick, W. A.; Pirrung, M. C.; Sohn, J. E.; Lampe, J. J. Org. Chem. 1980, 45, 1066. Anh, N. T.; Elkaïm, L.; Thanh, B. T.; Maurel, F.; Flament, J. P. Bull. Soc. Chim. Fr. 1992, 129, 468.
53. Zimmerman, H. E.; Traxler, M. D. J. Am. Chem. Soc. 1957, 79, 1920. See also: Kleschick, W. A.; Buse, C. T.; Heathcock, C. H. Ibid. 1977, 99, 247. Fellmann, P.; Dubois, J. E. Tetrahedron 1978, 34, 1349. Evans, D. A.; Vogel, E.; Nelson, J. V. J. Am. Chem. Soc. 1979, 101, 6120. Heathcock, C. H.; Buse, C. T.; Kleschick, W. A.; Pirrung, M. C.; Sohn, J. E.; Lampe, J. J. Org. Chem. 1980, 45, 1066. Anh, N. T.; Elkaïm, L.; Thanh, B. T.; Maurel, F.; Flament, J. P. Bull. Soc. Chim. Fr. 1992, 129, 468.
54. Evans, D. A.; Nelson, J. V.; Taber, T. R. Topics Stereochem. 1982, 31, 1.
55. Seebach, D.; Prelog, V. Angew. Chem., Int. Ed. Engl. 1982, 21, 654.
56. Roush, W. R. J. Org. Chem. 1991, 56, 4151.
57. Sevin, A. F.; Vogel, P. J. Org. Chem. 1994, 59, 5920. Kernen, P.; Vogel, P. Helv. Chim. Acta 1995, 78, 301.
58. Sevin, A. F.; Vogel, P. J. Org. Chem. 1994, 59, 5920. Kernen, P.; Vogel, P. Helv. Chim. Acta 1995, 78, 301.
59. Haneda, T.; Goekjian, P. G.; Kim, S. H.; Kishi, Y. J. Org. Chem. 1992, 57, 490. Ferritto, R.; Vogel, P. Tetrahedron: Asymmetry 1994, 5, 2077. Wei, A.; Boy, K. M.; Kishi, Y. J. Am. Chem. Soc. 1995, 117, 9432. Wei, A.; Haudrechy, A.; Audin, C.; Jun, H.-S.; Haudrechy-Bretel, N.; Kishi, Y. J. Org. Chem. 1995, 60, 2160. Berthault, P.; Birlirakis, N.; Rubinstenn, G.; Sinay, P.; Desvaux, H. J. J. Biomolecular NMR 1996, 8, 23.
60. Haneda, T.; Goekjian, P. G.; Kim, S. H.; Kishi, Y. J. Org. Chem. 1992, 57, 490. Ferritto, R.; Vogel, P. Tetrahedron: Asymmetry 1994, 5, 2077. Wei, A.; Boy, K. M.; Kishi, Y. J. Am. Chem. Soc. 1995, 117, 9432. Wei, A.; Haudrechy, A.; Audin, C.; Jun, H.-S.; Haudrechy-Bretel, N.; Kishi, Y. J. Org. Chem. 1995, 60, 2160. Berthault, P.; Birlirakis, N.; Rubinstenn, G.; Sinay, P.; Desvaux, H. J. J. Biomolecular NMR 1996, 8, 23.
61. Haneda, T.; Goekjian, P. G.; Kim, S. H.; Kishi, Y. J. Org. Chem. 1992, 57, 490. Ferritto, R.; Vogel, P. Tetrahedron: Asymmetry 1994, 5, 2077. Wei, A.; Boy, K. M.; Kishi, Y. J. Am. Chem. Soc. 1995, 117, 9432. Wei, A.; Haudrechy, A.; Audin, C.; Jun, H.-S.; Haudrechy-Bretel, N.; Kishi, Y. J. Org. Chem. 1995, 60, 2160. Berthault, P.; Birlirakis, N.; Rubinstenn, G.; Sinay, P.; Desvaux, H. J. J. Biomolecular NMR 1996, 8, 23.
62. Haneda, T.; Goekjian, P. G.; Kim, S. H.; Kishi, Y. J. Org. Chem. 1992, 57, 490. Ferritto, R.; Vogel, P. Tetrahedron: Asymmetry 1994, 5, 2077. Wei, A.; Boy, K. M.; Kishi, Y. J. Am. Chem. Soc. 1995, 117, 9432. Wei, A.; Haudrechy, A.; Audin, C.; Jun, H.-S.; Haudrechy-Bretel, N.; Kishi, Y. J. Org. Chem. 1995, 60, 2160. Berthault, P.; Birlirakis, N.; Rubinstenn, G.; Sinay, P.; Desvaux, H. J. J. Biomolecular NMR 1996, 8, 23.
63. Haneda, T.; Goekjian, P. G.; Kim, S. H.; Kishi, Y. J. Org. Chem. 1992, 57, 490. Ferritto, R.; Vogel, P. Tetrahedron: Asymmetry 1994, 5, 2077. Wei, A.; Boy, K. M.; Kishi, Y. J. Am. Chem. Soc. 1995, 117, 9432. Wei, A.; Haudrechy, A.; Audin, C.; Jun, H.-S.; Haudrechy-Bretel, N.; Kishi, Y. J. Org. Chem. 1995, 60, 2160. Berthault, P.; Birlirakis, N.; Rubinstenn, G.; Sinay, P.; Desvaux, H. J. J. Biomolecular NMR 1996, 8, 23.
64. Espinosa, J.-F.; Dietrich, H.; Martín-Lomas, M.; Schmidt, R. R., Jiménez-Barbero, J. Tetrahedron Lett. 1996, 37, 1467. Espinosa, J.-F.; Cañada, F. J.; Asensio, J. L.; Martín-Pastor, M.; Dietrich, H.; Martín-Lomas, M.; Schmidt, R. R.; Jiménez-Barbero, J. J. Am. Chem. Soc. 1996, 118, 10862.
65. Espinosa, J.-F.; Dietrich, H.; Martín-Lomas, M.; Schmidt, R. R., Jiménez-Barbero, J. Tetrahedron Lett. 1996, 37, 1467. Espinosa, J.-F.; Cañada, F. J.; Asensio, J. L.; Martín-Pastor, M.; Dietrich, H.; Martín-Lomas, M.; Schmidt, R. R.; Jiménez-Barbero, J. J. Am. Chem. Soc. 1996, 118, 10862.
66. Kraehenbuehl, K.; Vogel, P. Tetrahedron Lett. 1995, 36, 8595.
67. 1H NMR spectrum of this mixture.
68. Gasparini, F.; Vogel, P. J. Org. Chem. 1990, 55, 2451.
69. Springer, G. F. Science 1984, 224, 1198. MacLean, G. D., Longenecker, B. L. Semin. Cancer Biol. 1991, 2, 443. Samuel, J.; Nouaim, A. A.; MacLean, G. D.; Suresh, M. R.; Longenecker, B. M. Cancer Res. 1990, 250, 4801. Zhuang, D.; Yousef, S.; Dennis, J. W. Cancer Biochem. Biophys. 1991, 12, 185. Rabinovich, N. R.; McInnes, P.; Klein, D. L.; Hall, P. F. Science 1994, 265, 1401.
70. Springer, G. F. Science 1984, 224, 1198. MacLean, G. D., Longenecker, B. L. Semin. Cancer Biol. 1991, 2, 443. Samuel, J.; Nouaim, A. A.; MacLean, G. D.; Suresh, M. R.; Longenecker, B. M. Cancer Res. 1990, 250, 4801. Zhuang, D.; Yousef, S.; Dennis, J. W. Cancer Biochem. Biophys. 1991, 12, 185. Rabinovich, N. R.; McInnes, P.; Klein, D. L.; Hall, P. F. Science 1994, 265, 1401.
71. Springer, G. F. Science 1984, 224, 1198. MacLean, G. D., Longenecker, B. L. Semin. Cancer Biol. 1991, 2, 443. Samuel, J.; Nouaim, A. A.; MacLean, G. D.; Suresh, M. R.; Longenecker, B. M. Cancer Res. 1990, 250, 4801. Zhuang, D.; Yousef, S.; Dennis, J. W. Cancer Biochem. Biophys. 1991, 12, 185. Rabinovich, N. R.; McInnes, P.; Klein, D. L.; Hall, P. F. Science 1994, 265, 1401.
72. Springer, G. F. Science 1984, 224, 1198. MacLean, G. D., Longenecker, B. L. Semin. Cancer Biol. 1991, 2, 443. Samuel, J.; Nouaim, A. A.; MacLean, G. D.; Suresh, M. R.; Longenecker, B. M. Cancer Res. 1990, 250, 4801. Zhuang, D.; Yousef, S.; Dennis, J. W. Cancer Biochem. Biophys. 1991, 12, 185. Rabinovich, N. R.; McInnes, P.; Klein, D. L.; Hall, P. F. Science 1994, 265, 1401.
73. Springer, G. F. Science 1984, 224, 1198. MacLean, G. D., Longenecker, B. L. Semin. Cancer Biol. 1991, 2, 443. Samuel, J.; Nouaim, A. A.; MacLean, G. D.; Suresh, M. R.; Longenecker, B. M. Cancer Res. 1990, 250, 4801. Zhuang, D.; Yousef, S.; Dennis, J. W. Cancer Biochem. Biophys. 1991, 12, 185. Rabinovich, N. R.; McInnes, P.; Klein, D. L.; Hall, P. F. Science 1994, 265, 1401.
74. See, e.g.: MacLean, G. D.; Reddish, M.; Koganty, R. R.; Wong, T.; Gaudhi, S.; Smolenski, M.; Samuel, J.; Nabholtz, J. M.; Longenecker, B. M. Cancer Immunol. Immunother. 1993, 36, 215. See also: Hanessian, S.; Qiu, D.; Prabhanjan, H.; Reddy, G. V.; Lou, B. Can. J. Chem. 1906, 74, 1738.
75. See, e.g.: MacLean, G. D.; Reddish, M.; Koganty, R. R.; Wong, T.; Gaudhi, S.; Smolenski, M.; Samuel, J.; Nabholtz, J. M.; Longenecker, B. M. Cancer Immunol. Immunother. 1993, 36, 215. See also: Hanessian, S.; Qiu, D.; Prabhanjan, H.; Reddy, G. V.; Lou, B. Can. J. Chem. 1906, 74, 1738.