Stereoselective Addition of 2-Furyllithium and 2-Thiazolyllithium to Sugar Nitrones. Synthesis of Carbon-Linked Glycoglycines

Journal of Organic Chemistry

Volumn 62, Issue 16, 1997, Pages 5484-5496

  Dondoni, Alessandro ^a   Junquera, Federico ^b   Merchánt, Francisco Luis ^b   Merino, Pedro ^b   Scherrmann, Marie Christine ^a,c   Tejero, Tomas ^b  

^a UNIVERSITY OF FERRARA   (Italy)

^b UNIVERSITY OF ZARAGOZA   (Spain)

^c UNIVERSITÉ PARIS SACLAY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000997345     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970290a     Document Type: Article

References (76)

1. Rocchi, R.; Giormani, V. Chemistry and Biochemistry of Amino Acids, Peptides, and Proteins; Weinstein, B., Ed., M. Dekker: New York, 1983; p 35.
2. For compounds in which the amino acid moiety is linked to the anomeric carbon through at least one carbon-carbon bond, see: (a) Bischofberger, K.; Hall, R. H.; Jordaan, A. J. Chem. Soc. Chem. Commun. 1975, 806. (b) Hall, R. H.; Bischofberger, K.; Eitelman, S. J.; Jordaan, A. J. Chem. Soc., Perkin Trans. 1 1977, 743. (c) Simchen, G.; Pürkner, E. Synthesis 1990, 525. (d) Lieberknecht, A.; Schmidt, J.; Stezowski, J. Tetrahedron Lett. 1991, 32, 2113. (e) Petrus, L.; BeMiller, J. N. Carbohydr. Res. 1992, 230, 197. (f) Kessler, H.; Wittmann, V.; Köck, M.; Kottenhahn, M. Angew. Chem., Int. Ed. Engl. 1992, 31, 902. (g) Bertozzi, C. R.; Hoeprich, P. D.; Bednarski, M. D. J. Org. Chem. 1992, 57, 6092. (h) Gurjar, M. K.; Mainkar, A. S.; Syamala, M. Tetrahedron Asymmetry 1993, 4, 2343.
3. For compounds in which the amino acid moiety is linked to the anomeric carbon through at least one carbon-carbon bond, see: (a) Bischofberger, K.; Hall, R. H.; Jordaan, A. J. Chem. Soc. Chem. Commun. 1975, 806. (b) Hall, R. H.; Bischofberger, K.; Eitelman, S. J.; Jordaan, A. J. Chem. Soc., Perkin Trans. 1 1977, 743. (c) Simchen, G.; Pürkner, E. Synthesis 1990, 525. (d) Lieberknecht, A.; Schmidt, J.; Stezowski, J. Tetrahedron Lett. 1991, 32, 2113. (e) Petrus, L.; BeMiller, J. N. Carbohydr. Res. 1992, 230, 197. (f) Kessler, H.; Wittmann, V.; Köck, M.; Kottenhahn, M. Angew. Chem., Int. Ed. Engl. 1992, 31, 902. (g) Bertozzi, C. R.; Hoeprich, P. D.; Bednarski, M. D. J. Org. Chem. 1992, 57, 6092. (h) Gurjar, M. K.; Mainkar, A. S.; Syamala, M. Tetrahedron Asymmetry 1993, 4, 2343.
4. For compounds in which the amino acid moiety is linked to the anomeric carbon through at least one carbon-carbon bond, see: (a) Bischofberger, K.; Hall, R. H.; Jordaan, A. J. Chem. Soc. Chem. Commun. 1975, 806. (b) Hall, R. H.; Bischofberger, K.; Eitelman, S. J.; Jordaan, A. J. Chem. Soc., Perkin Trans. 1 1977, 743. (c) Simchen, G.; Pürkner, E. Synthesis 1990, 525. (d) Lieberknecht, A.; Schmidt, J.; Stezowski, J. Tetrahedron Lett. 1991, 32, 2113. (e) Petrus, L.; BeMiller, J. N. Carbohydr. Res. 1992, 230, 197. (f) Kessler, H.; Wittmann, V.; Köck, M.; Kottenhahn, M. Angew. Chem., Int. Ed. Engl. 1992, 31, 902. (g) Bertozzi, C. R.; Hoeprich, P. D.; Bednarski, M. D. J. Org. Chem. 1992, 57, 6092. (h) Gurjar, M. K.; Mainkar, A. S.; Syamala, M. Tetrahedron Asymmetry 1993, 4, 2343.
5. For compounds in which the amino acid moiety is linked to the anomeric carbon through at least one carbon-carbon bond, see: (a) Bischofberger, K.; Hall, R. H.; Jordaan, A. J. Chem. Soc. Chem. Commun. 1975, 806. (b) Hall, R. H.; Bischofberger, K.; Eitelman, S. J.; Jordaan, A. J. Chem. Soc., Perkin Trans. 1 1977, 743. (c) Simchen, G.; Pürkner, E. Synthesis 1990, 525. (d) Lieberknecht, A.; Schmidt, J.; Stezowski, J. Tetrahedron Lett. 1991, 32, 2113. (e) Petrus, L.; BeMiller, J. N. Carbohydr. Res. 1992, 230, 197. (f) Kessler, H.; Wittmann, V.; Köck, M.; Kottenhahn, M. Angew. Chem., Int. Ed. Engl. 1992, 31, 902. (g) Bertozzi, C. R.; Hoeprich, P. D.; Bednarski, M. D. J. Org. Chem. 1992, 57, 6092. (h) Gurjar, M. K.; Mainkar, A. S.; Syamala, M. Tetrahedron Asymmetry 1993, 4, 2343.
6. For compounds in which the amino acid moiety is linked to the anomeric carbon through at least one carbon-carbon bond, see: (a) Bischofberger, K.; Hall, R. H.; Jordaan, A. J. Chem. Soc. Chem. Commun. 1975, 806. (b) Hall, R. H.; Bischofberger, K.; Eitelman, S. J.; Jordaan, A. J. Chem. Soc., Perkin Trans. 1 1977, 743. (c) Simchen, G.; Pürkner, E. Synthesis 1990, 525. (d) Lieberknecht, A.; Schmidt, J.; Stezowski, J. Tetrahedron Lett. 1991, 32, 2113. (e) Petrus, L.; BeMiller, J. N. Carbohydr. Res. 1992, 230, 197. (f) Kessler, H.; Wittmann, V.; Köck, M.; Kottenhahn, M. Angew. Chem., Int. Ed. Engl. 1992, 31, 902. (g) Bertozzi, C. R.; Hoeprich, P. D.; Bednarski, M. D. J. Org. Chem. 1992, 57, 6092. (h) Gurjar, M. K.; Mainkar, A. S.; Syamala, M. Tetrahedron Asymmetry 1993, 4, 2343.
7. For compounds in which the amino acid moiety is linked to the anomeric carbon through at least one carbon-carbon bond, see: (a) Bischofberger, K.; Hall, R. H.; Jordaan, A. J. Chem. Soc. Chem. Commun. 1975, 806. (b) Hall, R. H.; Bischofberger, K.; Eitelman, S. J.; Jordaan, A. J. Chem. Soc., Perkin Trans. 1 1977, 743. (c) Simchen, G.; Pürkner, E. Synthesis 1990, 525. (d) Lieberknecht, A.; Schmidt, J.; Stezowski, J. Tetrahedron Lett. 1991, 32, 2113. (e) Petrus, L.; BeMiller, J. N. Carbohydr. Res. 1992, 230, 197. (f) Kessler, H.; Wittmann, V.; Köck, M.; Kottenhahn, M. Angew. Chem., Int. Ed. Engl. 1992, 31, 902. (g) Bertozzi, C. R.; Hoeprich, P. D.; Bednarski, M. D. J. Org. Chem. 1992, 57, 6092. (h) Gurjar, M. K.; Mainkar, A. S.; Syamala, M. Tetrahedron Asymmetry 1993, 4, 2343.
8. For compounds in which the amino acid moiety is linked to the anomeric carbon through at least one carbon-carbon bond, see: (a) Bischofberger, K.; Hall, R. H.; Jordaan, A. J. Chem. Soc. Chem. Commun. 1975, 806. (b) Hall, R. H.; Bischofberger, K.; Eitelman, S. J.; Jordaan, A. J. Chem. Soc., Perkin Trans. 1 1977, 743. (c) Simchen, G.; Pürkner, E. Synthesis 1990, 525. (d) Lieberknecht, A.; Schmidt, J.; Stezowski, J. Tetrahedron Lett. 1991, 32, 2113. (e) Petrus, L.; BeMiller, J. N. Carbohydr. Res. 1992, 230, 197. (f) Kessler, H.; Wittmann, V.; Köck, M.; Kottenhahn, M. Angew. Chem., Int. Ed. Engl. 1992, 31, 902. (g) Bertozzi, C. R.; Hoeprich, P. D.; Bednarski, M. D. J. Org. Chem. 1992, 57, 6092. (h) Gurjar, M. K.; Mainkar, A. S.; Syamala, M. Tetrahedron Asymmetry 1993, 4, 2343.
9. For compounds in which the amino acid moiety is linked to the anomeric carbon through at least one carbon-carbon bond, see: (a) Bischofberger, K.; Hall, R. H.; Jordaan, A. J. Chem. Soc. Chem. Commun. 1975, 806. (b) Hall, R. H.; Bischofberger, K.; Eitelman, S. J.; Jordaan, A. J. Chem. Soc., Perkin Trans. 1 1977, 743. (c) Simchen, G.; Pürkner, E. Synthesis 1990, 525. (d) Lieberknecht, A.; Schmidt, J.; Stezowski, J. Tetrahedron Lett. 1991, 32, 2113. (e) Petrus, L.; BeMiller, J. N. Carbohydr. Res. 1992, 230, 197. (f) Kessler, H.; Wittmann, V.; Köck, M.; Kottenhahn, M. Angew. Chem., Int. Ed. Engl. 1992, 31, 902. (g) Bertozzi, C. R.; Hoeprich, P. D.; Bednarski, M. D. J. Org. Chem. 1992, 57, 6092. (h) Gurjar, M. K.; Mainkar, A. S.; Syamala, M. Tetrahedron Asymmetry 1993, 4, 2343.
10. For compounds in which the anomeric carbon of a furanose or pyranose ring coincides with the central carbon of the amino acid moiety, see: (a) Burton, J. W.; Son, J. C.; Fairbanks, A. J.; Choi, S. S.; Taylor, H.; Watkin, D. J.; Winchester, B. G.; Fleet, G. W. J. Tetrahedron Lett. 1993, 34, 6119. (b) Dondoni, A.; Scherrmann, M.-C.; Marra, A.; Delépine, J.-L. J. Org. Chem. 1994, 59, 7517. (c) Estevez, J. C.; Estevez, R. J.; Ardron, H.; Wormald, M. R.; Brown, D.; Fleet, G. W. J. Tetrahedron Lett. 1994, 47, 8885. (d) Bichard, C. J. F.; Mitchell, E. P.; Wormald, M. R.; Watson, K. A.; Johnson, L. N.; Zographos, S. E.; Koutra, D. D.; Oikonomakos, N. G.; Fleet, G. W. J. Tetrahedron Lett. 1995, 36, 2145. (e) Brandstetter, T. W.; Kim, Y.; Son, J. C.; Taylor, H. M.; de Q. Lilley, P. M.; Watkin, D. J.; Johnson, L. N.; Oikonomakos, N. G.; Fleet, G. W. J.Tetrahedron Lett. 1995, 36, 2149. (f) Brandstetter, T. W.; de la Fuente, C.; Kim, Y.; Cooper, R. I.; Watkin, D. J.; Oikonomakos, N. G.; Johnson, L. N.; Fleet, G. W. J. Tetrahedron 1996, 32, 10711. (g) Brandstetter, T. W.; Wormald, M. R.; Dwek, R. A.; Butters, T. D.; Platt, F. M.; Tsitsanou, K. E.; Zographos, S. E.; Oikonomakos, N. G.; Fleet, G. W. J. Tetrahedron Asymmetry 1996, 7, 157. (h) Estevez, J. C.; Smith, M. D.; Lane, A. L.; Crook, S.; Watkin, D. J.; Besra, G. S.; Brennan, P. J.; Nash, R. J.; Fleet, G. W. J. Tetrahedron Asymmetry 1996, 7, 387.
11. For compounds in which the anomeric carbon of a furanose or pyranose ring coincides with the central carbon of the amino acid moiety, see: (a) Burton, J. W.; Son, J. C.; Fairbanks, A. J.; Choi, S. S.; Taylor, H.; Watkin, D. J.; Winchester, B. G.; Fleet, G. W. J. Tetrahedron Lett. 1993, 34, 6119. (b) Dondoni, A.; Scherrmann, M.-C.; Marra, A.; Delépine, J.-L. J. Org. Chem. 1994, 59, 7517. (c) Estevez, J. C.; Estevez, R. J.; Ardron, H.; Wormald, M. R.; Brown, D.; Fleet, G. W. J. Tetrahedron Lett. 1994, 47, 8885. (d) Bichard, C. J. F.; Mitchell, E. P.; Wormald, M. R.; Watson, K. A.; Johnson, L. N.; Zographos, S. E.; Koutra, D. D.; Oikonomakos, N. G.; Fleet, G. W. J. Tetrahedron Lett. 1995, 36, 2145. (e) Brandstetter, T. W.; Kim, Y.; Son, J. C.; Taylor, H. M.; de Q. Lilley, P. M.; Watkin, D. J.; Johnson, L. N.; Oikonomakos, N. G.; Fleet, G. W. J.Tetrahedron Lett. 1995, 36, 2149. (f) Brandstetter, T. W.; de la Fuente, C.; Kim, Y.; Cooper, R. I.; Watkin, D. J.; Oikonomakos, N. G.; Johnson, L. N.; Fleet, G. W. J. Tetrahedron 1996, 32, 10711. (g) Brandstetter, T. W.; Wormald, M. R.; Dwek, R. A.; Butters, T. D.; Platt, F. M.; Tsitsanou, K. E.; Zographos, S. E.; Oikonomakos, N. G.; Fleet, G. W. J. Tetrahedron Asymmetry 1996, 7, 157. (h) Estevez, J. C.; Smith, M. D.; Lane, A. L.; Crook, S.; Watkin, D. J.; Besra, G. S.; Brennan, P. J.; Nash, R. J.; Fleet, G. W. J. Tetrahedron Asymmetry 1996, 7, 387.
12. For compounds in which the anomeric carbon of a furanose or pyranose ring coincides with the central carbon of the amino acid moiety, see: (a) Burton, J. W.; Son, J. C.; Fairbanks, A. J.; Choi, S. S.; Taylor, H.; Watkin, D. J.; Winchester, B. G.; Fleet, G. W. J. Tetrahedron Lett. 1993, 34, 6119. (b) Dondoni, A.; Scherrmann, M.-C.; Marra, A.; Delépine, J.-L. J. Org. Chem. 1994, 59, 7517. (c) Estevez, J. C.; Estevez, R. J.; Ardron, H.; Wormald, M. R.; Brown, D.; Fleet, G. W. J. Tetrahedron Lett. 1994, 47, 8885. (d) Bichard, C. J. F.; Mitchell, E. P.; Wormald, M. R.; Watson, K. A.; Johnson, L. N.; Zographos, S. E.; Koutra, D. D.; Oikonomakos, N. G.; Fleet, G. W. J. Tetrahedron Lett. 1995, 36, 2145. (e) Brandstetter, T. W.; Kim, Y.; Son, J. C.; Taylor, H. M.; de Q. Lilley, P. M.; Watkin, D. J.; Johnson, L. N.; Oikonomakos, N. G.; Fleet, G. W. J.Tetrahedron Lett. 1995, 36, 2149. (f) Brandstetter, T. W.; de la Fuente, C.; Kim, Y.; Cooper, R. I.; Watkin, D. J.; Oikonomakos, N. G.; Johnson, L. N.; Fleet, G. W. J. Tetrahedron 1996, 32, 10711. (g) Brandstetter, T. W.; Wormald, M. R.; Dwek, R. A.; Butters, T. D.; Platt, F. M.; Tsitsanou, K. E.; Zographos, S. E.; Oikonomakos, N. G.; Fleet, G. W. J. Tetrahedron Asymmetry 1996, 7, 157. (h) Estevez, J. C.; Smith, M. D.; Lane, A. L.; Crook, S.; Watkin, D. J.; Besra, G. S.; Brennan, P. J.; Nash, R. J.; Fleet, G. W. J. Tetrahedron Asymmetry 1996, 7, 387.
13. For compounds in which the anomeric carbon of a furanose or pyranose ring coincides with the central carbon of the amino acid moiety, see: (a) Burton, J. W.; Son, J. C.; Fairbanks, A. J.; Choi, S. S.; Taylor, H.; Watkin, D. J.; Winchester, B. G.; Fleet, G. W. J. Tetrahedron Lett. 1993, 34, 6119. (b) Dondoni, A.; Scherrmann, M.-C.; Marra, A.; Delépine, J.-L. J. Org. Chem. 1994, 59, 7517. (c) Estevez, J. C.; Estevez, R. J.; Ardron, H.; Wormald, M. R.; Brown, D.; Fleet, G. W. J. Tetrahedron Lett. 1994, 47, 8885. (d) Bichard, C. J. F.; Mitchell, E. P.; Wormald, M. R.; Watson, K. A.; Johnson, L. N.; Zographos, S. E.; Koutra, D. D.; Oikonomakos, N. G.; Fleet, G. W. J. Tetrahedron Lett. 1995, 36, 2145. (e) Brandstetter, T. W.; Kim, Y.; Son, J. C.; Taylor, H. M.; de Q. Lilley, P. M.; Watkin, D. J.; Johnson, L. N.; Oikonomakos, N. G.; Fleet, G. W. J.Tetrahedron Lett. 1995, 36, 2149. (f) Brandstetter, T. W.; de la Fuente, C.; Kim, Y.; Cooper, R. I.; Watkin, D. J.; Oikonomakos, N. G.; Johnson, L. N.; Fleet, G. W. J. Tetrahedron 1996, 32, 10711. (g) Brandstetter, T. W.; Wormald, M. R.; Dwek, R. A.; Butters, T. D.; Platt, F. M.; Tsitsanou, K. E.; Zographos, S. E.; Oikonomakos, N. G.; Fleet, G. W. J. Tetrahedron Asymmetry 1996, 7, 157. (h) Estevez, J. C.; Smith, M. D.; Lane, A. L.; Crook, S.; Watkin, D. J.; Besra, G. S.; Brennan, P. J.; Nash, R. J.; Fleet, G. W. J. Tetrahedron Asymmetry 1996, 7, 387.
14. For compounds in which the anomeric carbon of a furanose or pyranose ring coincides with the central carbon of the amino acid moiety, see: (a) Burton, J. W.; Son, J. C.; Fairbanks, A. J.; Choi, S. S.; Taylor, H.; Watkin, D. J.; Winchester, B. G.; Fleet, G. W. J. Tetrahedron Lett. 1993, 34, 6119. (b) Dondoni, A.; Scherrmann, M.-C.; Marra, A.; Delépine, J.-L. J. Org. Chem. 1994, 59, 7517. (c) Estevez, J. C.; Estevez, R. J.; Ardron, H.; Wormald, M. R.; Brown, D.; Fleet, G. W. J. Tetrahedron Lett. 1994, 47, 8885. (d) Bichard, C. J. F.; Mitchell, E. P.; Wormald, M. R.; Watson, K. A.; Johnson, L. N.; Zographos, S. E.; Koutra, D. D.; Oikonomakos, N. G.; Fleet, G. W. J. Tetrahedron Lett. 1995, 36, 2145. (e) Brandstetter, T. W.; Kim, Y.; Son, J. C.; Taylor, H. M.; de Q. Lilley, P. M.; Watkin, D. J.; Johnson, L. N.; Oikonomakos, N. G.; Fleet, G. W. J.Tetrahedron Lett. 1995, 36, 2149. (f) Brandstetter, T. W.; de la Fuente, C.; Kim, Y.; Cooper, R. I.; Watkin, D. J.; Oikonomakos, N. G.; Johnson, L. N.; Fleet, G. W. J. Tetrahedron 1996, 32, 10711. (g) Brandstetter, T. W.; Wormald, M. R.; Dwek, R. A.; Butters, T. D.; Platt, F. M.; Tsitsanou, K. E.; Zographos, S. E.; Oikonomakos, N. G.; Fleet, G. W. J. Tetrahedron Asymmetry 1996, 7, 157. (h) Estevez, J. C.; Smith, M. D.; Lane, A. L.; Crook, S.; Watkin, D. J.; Besra, G. S.; Brennan, P. J.; Nash, R. J.; Fleet, G. W. J. Tetrahedron Asymmetry 1996, 7, 387.
15. For compounds in which the anomeric carbon of a furanose or pyranose ring coincides with the central carbon of the amino acid moiety, see: (a) Burton, J. W.; Son, J. C.; Fairbanks, A. J.; Choi, S. S.; Taylor, H.; Watkin, D. J.; Winchester, B. G.; Fleet, G. W. J. Tetrahedron Lett. 1993, 34, 6119. (b) Dondoni, A.; Scherrmann, M.-C.; Marra, A.; Delépine, J.-L. J. Org. Chem. 1994, 59, 7517. (c) Estevez, J. C.; Estevez, R. J.; Ardron, H.; Wormald, M. R.; Brown, D.; Fleet, G. W. J. Tetrahedron Lett. 1994, 47, 8885. (d) Bichard, C. J. F.; Mitchell, E. P.; Wormald, M. R.; Watson, K. A.; Johnson, L. N.; Zographos, S. E.; Koutra, D. D.; Oikonomakos, N. G.; Fleet, G. W. J. Tetrahedron Lett. 1995, 36, 2145. (e) Brandstetter, T. W.; Kim, Y.; Son, J. C.; Taylor, H. M.; de Q. Lilley, P. M.; Watkin, D. J.; Johnson, L. N.; Oikonomakos, N. G.; Fleet, G. W. J.Tetrahedron Lett. 1995, 36, 2149. (f) Brandstetter, T. W.; de la Fuente, C.; Kim, Y.; Cooper, R. I.; Watkin, D. J.; Oikonomakos, N. G.; Johnson, L. N.; Fleet, G. W. J. Tetrahedron 1996, 32, 10711. (g) Brandstetter, T. W.; Wormald, M. R.; Dwek, R. A.; Butters, T. D.; Platt, F. M.; Tsitsanou, K. E.; Zographos, S. E.; Oikonomakos, N. G.; Fleet, G. W. J. Tetrahedron Asymmetry 1996, 7, 157. (h) Estevez, J. C.; Smith, M. D.; Lane, A. L.; Crook, S.; Watkin, D. J.; Besra, G. S.; Brennan, P. J.; Nash, R. J.; Fleet, G. W. J. Tetrahedron Asymmetry 1996, 7, 387.
16. For compounds in which the anomeric carbon of a furanose or pyranose ring coincides with the central carbon of the amino acid moiety, see: (a) Burton, J. W.; Son, J. C.; Fairbanks, A. J.; Choi, S. S.; Taylor, H.; Watkin, D. J.; Winchester, B. G.; Fleet, G. W. J. Tetrahedron Lett. 1993, 34, 6119. (b) Dondoni, A.; Scherrmann, M.-C.; Marra, A.; Delépine, J.-L. J. Org. Chem. 1994, 59, 7517. (c) Estevez, J. C.; Estevez, R. J.; Ardron, H.; Wormald, M. R.; Brown, D.; Fleet, G. W. J. Tetrahedron Lett. 1994, 47, 8885. (d) Bichard, C. J. F.; Mitchell, E. P.; Wormald, M. R.; Watson, K. A.; Johnson, L. N.; Zographos, S. E.; Koutra, D. D.; Oikonomakos, N. G.; Fleet, G. W. J. Tetrahedron Lett. 1995, 36, 2145. (e) Brandstetter, T. W.; Kim, Y.; Son, J. C.; Taylor, H. M.; de Q. Lilley, P. M.; Watkin, D. J.; Johnson, L. N.; Oikonomakos, N. G.; Fleet, G. W. J.Tetrahedron Lett. 1995, 36, 2149. (f) Brandstetter, T. W.; de la Fuente, C.; Kim, Y.; Cooper, R. I.; Watkin, D. J.; Oikonomakos, N. G.; Johnson, L. N.; Fleet, G. W. J. Tetrahedron 1996, 32, 10711. (g) Brandstetter, T. W.; Wormald, M. R.; Dwek, R. A.; Butters, T. D.; Platt, F. M.; Tsitsanou, K. E.; Zographos, S. E.; Oikonomakos, N. G.; Fleet, G. W. J. Tetrahedron Asymmetry 1996, 7, 157. (h) Estevez, J. C.; Smith, M. D.; Lane, A. L.; Crook, S.; Watkin, D. J.; Besra, G. S.; Brennan, P. J.; Nash, R. J.; Fleet, G. W. J. Tetrahedron Asymmetry 1996, 7, 387.
17. For compounds in which the anomeric carbon of a furanose or pyranose ring coincides with the central carbon of the amino acid moiety, see: (a) Burton, J. W.; Son, J. C.; Fairbanks, A. J.; Choi, S. S.; Taylor, H.; Watkin, D. J.; Winchester, B. G.; Fleet, G. W. J. Tetrahedron Lett. 1993, 34, 6119. (b) Dondoni, A.; Scherrmann, M.-C.; Marra, A.; Delépine, J.-L. J. Org. Chem. 1994, 59, 7517. (c) Estevez, J. C.; Estevez, R. J.; Ardron, H.; Wormald, M. R.; Brown, D.; Fleet, G. W. J. Tetrahedron Lett. 1994, 47, 8885. (d) Bichard, C. J. F.; Mitchell, E. P.; Wormald, M. R.; Watson, K. A.; Johnson, L. N.; Zographos, S. E.; Koutra, D. D.; Oikonomakos, N. G.; Fleet, G. W. J. Tetrahedron Lett. 1995, 36, 2145. (e) Brandstetter, T. W.; Kim, Y.; Son, J. C.; Taylor, H. M.; de Q. Lilley, P. M.; Watkin, D. J.; Johnson, L. N.; Oikonomakos, N. G.; Fleet, G. W. J.Tetrahedron Lett. 1995, 36, 2149. (f) Brandstetter, T. W.; de la Fuente, C.; Kim, Y.; Cooper, R. I.; Watkin, D. J.; Oikonomakos, N. G.; Johnson, L. N.; Fleet, G. W. J. Tetrahedron 1996, 32, 10711. (g) Brandstetter, T. W.; Wormald, M. R.; Dwek, R. A.; Butters, T. D.; Platt, F. M.; Tsitsanou, K. E.; Zographos, S. E.; Oikonomakos, N. G.; Fleet, G. W. J. Tetrahedron Asymmetry 1996, 7, 157. (h) Estevez, J. C.; Smith, M. D.; Lane, A. L.; Crook, S.; Watkin, D. J.; Besra, G. S.; Brennan, P. J.; Nash, R. J.; Fleet, G. W. J. Tetrahedron Asymmetry 1996, 7, 387.
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32. (g) Bouifraden, S.; Hadrami, M. El.; Ittobane, N.; Lavergne, J.-P.; Viallefont, Ph. Synth. Commun. 1993, 23, 2559.
33. (h) Chen, A.; Savage, I.; Thomas, E. J.; Wilson, P. D. Tetrahedron Lett. 1993, 34, 6769.
34. (a) Bessodes, M.; Komiotis, D.; Antonakis, K. J. Chem. Soc., Perkin Trans. 1 1989, 41.
35. (b) Simchen, G.; Purkner, E. Synthesis 1990, 525.
36. (c) Colombo, L.; Casiraghi, G.; Pittalis, A. J. Org. Chem. 1991, 56, 3897.
37. (d) Casiraghi, G.; Colombo, L.; Rassu, G.; Spanu, P. J. Org. Chem. 1991, 56, 6523.
38. (e) Hadrami, M. El.; Lavergne, J.-P.; Viallefont, Ph.; Chiaroni, A.; Riche, C.; Hasnaoui, A. Synth. Commun. 1993, 23, 157.
39. Dondoni, A.; Franco, S.; Junquera, F.; Merchan, F. L.; Merino, P.; Tejero, T.; Bertolasi, V. Chem. Eur. J. 1995, 1, 505.
40. Dondoni, A.; Junquera, F.; Merchan, F. L.; Merino, P.; Tejero, T. Synthesis 1994, 1450.
41. It is worth pointing out that the trivial name C-glycosyl α-amino acid appears appropriate only for compounds wherein the amino acid moiety is linked to the sugar anomeric carbon.
42. In related research works we have experienced various oxidizing agents, all operating under mild and almost neutral reaction conditions. See: ref 12 and Dondoni, A.; Franco, S.; Merchan, F. L.; Merino, P.; Tejero, T. Tetrahedron Lett. 1993, 34, 5479. Dondoni, A.; Perrone, D.; Merino, P. J. Chem. Soc., Chem. Commun. 1991, 1313.
43. In related research works we have experienced various oxidizing agents, all operating under mild and almost neutral reaction conditions. See: ref 12 and Dondoni, A.; Franco, S.; Merchan, F. L.; Merino, P.; Tejero, T. Tetrahedron Lett. 1993, 34, 5479. Dondoni, A.; Perrone, D.; Merino, P. J. Chem. Soc., Chem. Commun. 1991, 1313.
44. 4: Mukaiyama, T. Tsuzuki, R.; Kato, J. Chem. Lett. 1985, 837. Danishefsky, S. J.; Pearson, W. H.; Segmuller, B. E. J. Am. Chem. Soc. 1985, 107, 1280. Danishefsky, S. J.; DeNinno, M. P.; Chen, S. J. Am. Chem. Soc. 1988, 110, 3929. Poss, H. A.; Reid, J. A. Tetrahedron Lett. 1992, 33, 1411. Marshall, J. A.; Luke, J. P. J. Org. Chem. 1993, 58, 6229.
45. 4: Mukaiyama, T. Tsuzuki, R.; Kato, J. Chem. Lett. 1985, 837. Danishefsky, S. J.; Pearson, W. H.; Segmuller, B. E. J. Am. Chem. Soc. 1985, 107, 1280. Danishefsky, S. J.; DeNinno, M. P.; Chen, S. J. Am. Chem. Soc. 1988, 110, 3929. Poss, H. A.; Reid, J. A. Tetrahedron Lett. 1992, 33, 1411. Marshall, J. A.; Luke, J. P. J. Org. Chem. 1993, 58, 6229.
46. 4: Mukaiyama, T. Tsuzuki, R.; Kato, J. Chem. Lett. 1985, 837. Danishefsky, S. J.; Pearson, W. H.; Segmuller, B. E. J. Am. Chem. Soc. 1985, 107, 1280. Danishefsky, S. J.; DeNinno, M. P.; Chen, S. J. Am. Chem. Soc. 1988, 110, 3929. Poss, H. A.; Reid, J. A. Tetrahedron Lett. 1992, 33, 1411. Marshall, J. A.; Luke, J. P. J. Org. Chem. 1993, 58, 6229.
47. 4: Mukaiyama, T. Tsuzuki, R.; Kato, J. Chem. Lett. 1985, 837. Danishefsky, S. J.; Pearson, W. H.; Segmuller, B. E. J. Am. Chem. Soc. 1985, 107, 1280. Danishefsky, S. J.; DeNinno, M. P.; Chen, S. J. Am. Chem. Soc. 1988, 110, 3929. Poss, H. A.; Reid, J. A. Tetrahedron Lett. 1992, 33, 1411. Marshall, J. A.; Luke, J. P. J. Org. Chem. 1993, 58, 6229.
48. 4: Mukaiyama, T. Tsuzuki, R.; Kato, J. Chem. Lett. 1985, 837. Danishefsky, S. J.; Pearson, W. H.; Segmuller, B. E. J. Am. Chem. Soc. 1985, 107, 1280. Danishefsky, S. J.; DeNinno, M. P.; Chen, S. J. Am. Chem. Soc. 1988, 110, 3929. Poss, H. A.; Reid, J. A. Tetrahedron Lett. 1992, 33, 1411. Marshall, J. A.; Luke, J. P. J. Org. Chem. 1993, 58, 6229.
49. 4: Mukaiyama, T. Tsuzuki, R.; Kato, J. Chem. Lett. 1985, 837. Danishefsky, S. J.; Pearson, W. H.; Segmuller, B. E. J. Am. Chem. Soc. 1985, 107, 1280. Danishefsky, S. J.; DeNinno, M. P.; Chen, S. J. Am. Chem. Soc. 1988, 110, 3929. Poss, H. A.; Reid, J. A. Tetrahedron Lett. 1992, 33, 1411. Marshall, J. A.; Luke, J. P. J. Org. Chem. 1993, 58, 6229.
50. 4: Mukaiyama, T. Tsuzuki, R.; Kato, J. Chem. Lett. 1985, 837. Danishefsky, S. J.; Pearson, W. H.; Segmuller, B. E. J. Am. Chem. Soc. 1985, 107, 1280. Danishefsky, S. J.; DeNinno, M. P.; Chen, S. J. Am. Chem. Soc. 1988, 110, 3929. Poss, H. A.; Reid, J. A. Tetrahedron Lett. 1992, 33, 1411. Marshall, J. A.; Luke, J. P. J. Org. Chem. 1993, 58, 6229.
51. 4: Mukaiyama, T. Tsuzuki, R.; Kato, J. Chem. Lett. 1985, 837. Danishefsky, S. J.; Pearson, W. H.; Segmuller, B. E. J. Am. Chem. Soc. 1985, 107, 1280. Danishefsky, S. J.; DeNinno, M. P.; Chen, S. J. Am. Chem. Soc. 1988, 110, 3929. Poss, H. A.; Reid, J. A. Tetrahedron Lett. 1992, 33, 1411. Marshall, J. A.; Luke, J. P. J. Org. Chem. 1993, 58, 6229.
52. 4: Mukaiyama, T. Tsuzuki, R.; Kato, J. Chem. Lett. 1985, 837. Danishefsky, S. J.; Pearson, W. H.; Segmuller, B. E. J. Am. Chem. Soc. 1985, 107, 1280. Danishefsky, S. J.; DeNinno, M. P.; Chen, S. J. Am. Chem. Soc. 1988, 110, 3929. Poss, H. A.; Reid, J. A. Tetrahedron Lett. 1992, 33, 1411. Marshall, J. A.; Luke, J. P. J. Org. Chem. 1993, 58, 6229.
53. Dondoni, A.; Franco, S.; Junquera, F.; Merchan, F. L.; Merino, P.; Tejero, T. Synth. Commun. 1994, 23, 2537.
54. The complexation as in the structure shown below exposes the opposite nitrone face to the attack of 1.
55. Murahashi, S.-I. Angew. Chem., Int. Ed. Engl. 1995, 34, 2443.
56. 3) δ: 1.32 (s, 3 H), 1.35 (s, 3 H), 3.14 (s, 3 H), 4.61 (m, 2 H), 4.84 (d, 1 H, J = 8.6 Hz), 4.96 (s, 1 H), 4.99 (d, 1 H, J = 6.1 Hz), 6.38 (m, 2 H), 7.30 (m, 5 H), 7.79 (m, 1 H), 8.20 (s, 1 H).
57. 4, see: Schuda, P. F.; Cichowicz, M. B.; Heimann, M. R. Tetrahedron Lett. 1983, 24, 3829.
58. 4, see: Schuda, P. F.; Cichowicz, M. B.; Heimann, M. R. Tetrahedron Lett. 1983, 24, 3829.
59. 4 was irradiated in both 7a and 7b. These data indicated the spatial disposition shown below. The configurational assignment based on NOE was confirmed by the total synthesis of thymine polyoxin C starting from 7b. See: Dondoni, A.; Junquera, F.; Merchan, F. L.; Merino, P.; Tejero, T. Tetrahedron Lett. 1994, 35, 9439 and the accompanying paper. Equation presented.
60. The X-ray crystal analyses have been performed by one of us (P.M.) at the University of Zaragoza. Atomic coordinates, bond lengths and angles, thermal parameters, and structure factors for compounds 9b, 12b, and 35b have been deposited at the Cambridge Crystallographic Data Center, 12 Union Road, Cambridge, CB2, 1EZ, UK. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Center. Some crystal data of these compounds and the relevant informations for their determinations are given in the Experimental Section.
61. Ottenheim, H. C. J.; Herscheid, J. D. M. Chem. Rev. 1986, 86, 697.
62. For some earlier examples, see ref 2a,b.
63. Dondoni, A.; Scherrmann, M.-C. J. Org. Chem. 1994, 59, 6404.
64. We have previously commented on the various inconveniences that are encountered with the direct conversion of the thiazole ring into carboxylic group by oxidative cleavage with different reagents (Dondoni, A.; Marra, A.; Merino, P. J. Am. Chem. Soc. 1994, 116, 3324). On the other hand the synthesis of carboxylic acids via thiazole-to-formyl deblocking and subsequent oxidation under mild and neutral conditions is rewarded by high yields and compatibility of the method with different protective groups and various structural arrays. See also: Dondoni, A.; Perrone, D. Synthesis 1993, 1162. Dondoni, A.; Scherrmann, M.-C. Marra, A.; Delépine, J.-L. J. Org. Chem. 1994, 59, 7517. Dondoni, A.; Boscarato, A.; Marra, A. Tetrahedron Asymmetry 1994, 5, 2209. Dondoni, A.; Perrone, D.; Semola, T. Synthesis 1995, 181. Dondoni, A.; Marra, A.; Rojo, I.; Scherrmann, M.-C. Tetrahedron 1996, 52, 3057. Marra, A.; Dondoni, A.; Sansone, F. J. Org. Chem. 1996, 61, 5155.
65. We have previously commented on the various inconveniences that are encountered with the direct conversion of the thiazole ring into carboxylic group by oxidative cleavage with different reagents (Dondoni, A.; Marra, A.; Merino, P. J. Am. Chem. Soc. 1994, 116, 3324). On the other hand the synthesis of carboxylic acids via thiazole-to-formyl deblocking and subsequent oxidation under mild and neutral conditions is rewarded by high yields and compatibility of the method with different protective groups and various structural arrays. See also: Dondoni, A.; Perrone, D. Synthesis 1993, 1162. Dondoni, A.; Scherrmann, M.-C. Marra, A.; Delépine, J.-L. J. Org. Chem. 1994, 59, 7517. Dondoni, A.; Boscarato, A.; Marra, A. Tetrahedron Asymmetry 1994, 5, 2209. Dondoni, A.; Perrone, D.; Semola, T. Synthesis 1995, 181. Dondoni, A.; Marra, A.; Rojo, I.; Scherrmann, M.-C. Tetrahedron 1996, 52, 3057. Marra, A.; Dondoni, A.; Sansone, F. J. Org. Chem. 1996, 61, 5155.
66. We have previously commented on the various inconveniences that are encountered with the direct conversion of the thiazole ring into carboxylic group by oxidative cleavage with different reagents (Dondoni, A.; Marra, A.; Merino, P. J. Am. Chem. Soc. 1994, 116, 3324). On the other hand the synthesis of carboxylic acids via thiazole-to-formyl deblocking and subsequent oxidation under mild and neutral conditions is rewarded by high yields and compatibility of the method with different protective groups and various structural arrays. See also: Dondoni, A.; Perrone, D. Synthesis 1993, 1162. Dondoni, A.; Scherrmann, M.-C. Marra, A.; Delépine, J.-L. J. Org. Chem. 1994, 59, 7517. Dondoni, A.; Boscarato, A.; Marra, A. Tetrahedron Asymmetry 1994, 5, 2209. Dondoni, A.; Perrone, D.; Semola, T. Synthesis 1995, 181. Dondoni, A.; Marra, A.; Rojo, I.; Scherrmann, M.-C. Tetrahedron 1996, 52, 3057. Marra, A.; Dondoni, A.; Sansone, F. J. Org. Chem. 1996, 61, 5155.
67. We have previously commented on the various inconveniences that are encountered with the direct conversion of the thiazole ring into carboxylic group by oxidative cleavage with different reagents (Dondoni, A.; Marra, A.; Merino, P. J. Am. Chem. Soc. 1994, 116, 3324). On the other hand the synthesis of carboxylic acids via thiazole-to-formyl deblocking and subsequent oxidation under mild and neutral conditions is rewarded by high yields and compatibility of the method with different protective groups and various structural arrays. See also: Dondoni, A.; Perrone, D. Synthesis 1993, 1162. Dondoni, A.; Scherrmann, M.-C. Marra, A.; Delépine, J.-L. J. Org. Chem. 1994, 59, 7517. Dondoni, A.; Boscarato, A.; Marra, A. Tetrahedron Asymmetry 1994, 5, 2209. Dondoni, A.; Perrone, D.; Semola, T. Synthesis 1995, 181. Dondoni, A.; Marra, A.; Rojo, I.; Scherrmann, M.-C. Tetrahedron 1996, 52, 3057. Marra, A.; Dondoni, A.; Sansone, F. J. Org. Chem. 1996, 61, 5155.
68. We have previously commented on the various inconveniences that are encountered with the direct conversion of the thiazole ring into carboxylic group by oxidative cleavage with different reagents (Dondoni, A.; Marra, A.; Merino, P. J. Am. Chem. Soc. 1994, 116, 3324). On the other hand the synthesis of carboxylic acids via thiazole-to-formyl deblocking and subsequent oxidation under mild and neutral conditions is rewarded by high yields and compatibility of the method with different protective groups and various structural arrays. See also: Dondoni, A.; Perrone, D. Synthesis 1993, 1162. Dondoni, A.; Scherrmann, M.-C. Marra, A.; Delépine, J.-L. J. Org. Chem. 1994, 59, 7517. Dondoni, A.; Boscarato, A.; Marra, A. Tetrahedron Asymmetry 1994, 5, 2209. Dondoni, A.; Perrone, D.; Semola, T. Synthesis 1995, 181. Dondoni, A.; Marra, A.; Rojo, I.; Scherrmann, M.-C. Tetrahedron 1996, 52, 3057. Marra, A.; Dondoni, A.; Sansone, F. J. Org. Chem. 1996, 61, 5155.
69. We have previously commented on the various inconveniences that are encountered with the direct conversion of the thiazole ring into carboxylic group by oxidative cleavage with different reagents (Dondoni, A.; Marra, A.; Merino, P. J. Am. Chem. Soc. 1994, 116, 3324). On the other hand the synthesis of carboxylic acids via thiazole-to-formyl deblocking and subsequent oxidation under mild and neutral conditions is rewarded by high yields and compatibility of the method with different protective groups and various structural arrays. See also: Dondoni, A.; Perrone, D. Synthesis 1993, 1162. Dondoni, A.; Scherrmann, M.-C. Marra, A.; Delépine, J.-L. J. Org. Chem. 1994, 59, 7517. Dondoni, A.; Boscarato, A.; Marra, A. Tetrahedron Asymmetry 1994, 5, 2209. Dondoni, A.; Perrone, D.; Semola, T. Synthesis 1995, 181. Dondoni, A.; Marra, A.; Rojo, I.; Scherrmann, M.-C. Tetrahedron 1996, 52, 3057. Marra, A.; Dondoni, A.; Sansone, F. J. Org. Chem. 1996, 61, 5155.
70. We have previously commented on the various inconveniences that are encountered with the direct conversion of the thiazole ring into carboxylic group by oxidative cleavage with different reagents (Dondoni, A.; Marra, A.; Merino, P. J. Am. Chem. Soc. 1994, 116, 3324). On the other hand the synthesis of carboxylic acids via thiazole-to-formyl deblocking and subsequent oxidation under mild and neutral conditions is rewarded by high yields and compatibility of the method with different protective groups and various structural arrays. See also: Dondoni, A.; Perrone, D. Synthesis 1993, 1162. Dondoni, A.; Scherrmann, M.-C. Marra, A.; Delépine, J.-L. J. Org. Chem. 1994, 59, 7517. Dondoni, A.; Boscarato, A.; Marra, A. Tetrahedron Asymmetry 1994, 5, 2209. Dondoni, A.; Perrone, D.; Semola, T. Synthesis 1995, 181. Dondoni, A.; Marra, A.; Rojo, I.; Scherrmann, M.-C. Tetrahedron 1996, 52, 3057. Marra, A.; Dondoni, A.; Sansone, F. J. Org. Chem. 1996, 61, 5155.
71. Dondoni, A.; Marra, A.; Perrone, D. J. Org. Chem. 1993, 58, 275.
72. Dalcanale, E.; Montanari, F. J. Org. Chem. 1986, 51, 567.
73. Merchan, F. L.; Merino, P.; Rojo, I.; Tejero, T., Dondoni, A. Tetrahedron: Asymmetry 1995, 6, 2145.
74. Tejero, T.; Franco, S.; Junquera, F.; Lanaspa, A.; Merchan, F. L.; Merino, P.; Rojo, I. Tetrahedron: Asymmetry 1996, 7, 1529.
75. Shriver, D. F.; Dredzon, M. A. The Manipulation of Air-Sensitive Compounds; 2nd ed.; Wiley-Interscience: New York, 1986.
76. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals, 3rd ed.; Pergamon: Oxford, 1988.