Synthesis of highly condensed polycyclic carbohydrates by reaction of a spirocyclic enamino sulfonate derived from D-xylofuranose with bifunctional reagents

Journal of Organic Chemistry

Volumn 72, Issue 25, 2007, Pages 9713-9721

  Cordeiro, Alessandra ^a   Jimeno, María Luisa ^b   Maestro, Miguel A ^c   Camarasa, María José ^a   Quesada, Ernesto ^a   San Félix, Ana ^a  

^a INSTITUTO DE QUÍMICA MÉDICA   (Spain)

^b CSIC Centro de Quimica Organica Lora Tamayo CENQUIOR   (Spain)

^c UNIVERSITY OF A CORUÑA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIZATION; NUCLEAR MAGNETIC RESONANCE; NUCLEOPHILES; SUGAR (SUCROSE); SYNTHESIS (CHEMICAL); X RAY DIFFRACTION ANALYSIS;

BIFUNCTIONAL REAGENTS; D-XYLOFURANOSE; POLYCYCLIC CARBOHYDRATES; SPIROCYCLIC ENAMINO SULFONATE;

CARBOHYDRATES;

CARBOHYDRATE DERIVATIVE; FURAN DERIVATIVE; POLYCYCLIC HYDROCARBON; REAGENT; SULFONIC ACID DERIVATIVE; XYLOSE;

ARTICLE; CARBOHYDRATE SYNTHESIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; NUCLEAR MAGNETIC RESONANCE; POLYMERIZATION; STEREOSPECIFICITY; SUBSTITUTION REACTION; X RAY DIFFRACTION;

ALKANESULFONATES; CARBOHYDRATES; CRYSTALLOGRAPHY, X-RAY; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; REFERENCE STANDARDS; SPIRO COMPOUNDS; STEREOISOMERISM; XYLOSE;

EID: 36849069446     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo701775a     Document Type: Article

References (38)

1. (a) Hanessian, S. In Total Synthesis of Natural Products; The "Chiron" approach; Organic Chemistry Series; Pergamon: Oxford, UK, 1983; Vol. 3.
2. (b) For a review see: Nicolau, K. C.; Mitchell, H. J. Angew. Chem., Int. Ed. 2001, 40, 1576.
3. (a) Sears, P.; Mitchell, H. J. Angew. Chem., Int. Ed. 1999, 38, 2300.
4. (b) Cipolla, L.; Peri, F.; Ferla, B. L.; Redaelli, C.; Nicotra, F. Curr. Org. Synth. 2005, 2, 153.
5. Nicolau, K. C.; Trujillo, J. I.; Chibale, K. Tetrahedron 1997, 53, 8751.
6. Gruner, S. A. W.; Locardi, E.; Lohof, E.; Kessler, H. Chem. Rev. 2002, 102, 491.
7. Chakraborty, T. K.; Srinivasu, P.; Tapadar, S.; Mohan, B. K. J. Chem. Sci. 2004, 116, 187.
8. (a) Nicolau, K. C.; Salvino, J. M.; Raynor, K.; Pietranico, S.; Reisine, T.; Freidinger, R. M.; Hirschmann, R. In Peptides: Chemical Structure and Biology; Marshall, G. R., Ed.; Escom: Leiden, The Netherlands, 1990; pp 881-884.
9. (b) Hirschman, R.; Hynes, J., Jr.; Cichy-Knight, M. A.; van Rijn, R. D.; Sprengeler, P. A.; Spoors, P. G.; Schakespeare, W. C.; Pietronico-Cole, S.; Barbosa, J.; Liu, J.; Yao, W.; Rohrer, S.; Smith, A. B., III J. Med. Chem. 1998, 41, 1382.
10. (c) Hirschman, R.; Wenquing, Y.; Cascieri, M.; Strader, C. D.; Maecheler, L.; Cichy-Knight, M. A.; Hynes, J., Jr.; van Rijn, R. D.; Sprengeler, P.; Smith, A. B., III J. Med. Chem. 1996, 39, 2441.
11. (d) Hirshmann, R.; Nicolau, K. C.; Pietranico, S.; Leahy, E. M.; Salvino, J.; Arison, B.; Cichy, M. A.; Spoors, P. G.; Shakespeare, W. C.; Sprengeler, P. A.; Hamley, P.; Smith, A. B., III; Reisine, T.; Raynor, K.; Maecheler, L.; Donadson, C.; Vale, W.; Freidinger, R. M.; Cascieri, M. R.; Strader, C. D. J. Am. Chem. Soc. 1993, 115, 12550.
12. Meutermans, W.; Le, G. T.; Becker, B. Med. Chem. Med. 2006, 1, 1164.
13. (a) Dinh, T. Q.; Smith, C. D.; Du, X.; Armstrong, W. J. Med. Chem. 1998, 41, 981.
14. (b) Moitessier, N.; Dufour, S.; Chretien, F.; Thiery, J. P.; Maigret, B.; Chapleur, Y. Bioorg. Med. Chem. 2001, 9, 511.
15. (a) Wunberg, T.; Kallus, C.; Opatz, T.; Henke, S.; Schmidt, W.; Kunz, H. Angew. Chem. 1998, 110, 2620;
16. Angew. Chem., Int. Ed. 1998, 37, 2503.
17. (b) Timmer, M. S. M.; Verdoes, M.; Sliedregt, L. A. J. M.; van der Marel, G., A.; van Boom, J. H.; Overkleeft, H. S. J. Org. Chem 2003, 68, 9406.
18. (a) Gruner, S. A. W.; Locardi, E.; Lohof, E.; Kessler, H. Chem. Rev. 2002, 102, 491.
19. For selected recent examples, see: (b) Bastida, A.; Hidalgo, A.; Chiara, J. L.; Torrado, M.; Corzana, F.; Pérez-Cañadillas, J. M.; Groves, P.; García-Junceda, E.; González, C.; Jiménez-Barbero, J.; Asensio, J. L. J. Am. Chem. Soc. 2006, 128, 100.
20. (c) Cipolla, L.; Forni, E.; Jiménez-Barbero, J.; Nicotra, F. Chem. Eur. J. 2002, 8, 3976.
21. (d) Sinou, D.; Bedjeguelal, K. J. Carbohydr. Chem. 2001, 20, 335.
22. (e) Hirschman, R.; Ducry, L.; Smith, A. B., III J. Org. Chem. 2000, 65, 8307.
23. (f) Banerjee, S.; Ghosh, S. J. Org. Chem. 2003, 68, 3981.
24. (g) Tripathi, S; Singha, K.; Achari, B; Mandal, S. B. Tetrahedron 2004, 4959.
25. Cordeiro, A.; Quesada, E.; Bonache, M. C.; Velázquez, S.; Camarasa, M. J.; San-Félix, A. J. Org. Chem. 2006, 71, 7224.
26. Hollowood, C. J.; Yamanoi, S.; Ley, S. V. Org. Biomol. Chem. 2003, 1, 1664.
27. Hurd, R. E.; John, B. K. J. Magn. Reson. 1991, 91, 1991.
28. Kay, L. E.; Keifer, P.; Saarinen, T. J. Am. Chem. Soc. 1992, 114, 10663.
29. 16
30. IUPAC nomenclature home page: http://www.chem.qmul.ac.uk/iupac/.
31. HyperChem, Release 5.1, Windows Molecular Modelling System; HyperCube: Waterloo, Ontario, Canada, 1997.
32. Tarköy, M.; Bolli, M.; Schweizer, B.; Leumann, C. Helv. Chim. Acta 1993, 76, 481.
33. Tronchet, J. M. J.; Brenas, L.; Barbalat-Rey, F.; Zsély, M.; Geoffroy, M. Nucleosides Nucleotides 1998, 17, 1019.
34. Pineda Molas, M.; Matheu, M. I.; Castillón, S. Tetrahedron 1999, 55, 14649.
35. (a) Altana, C.; Sundaralingam, M. J. Am. Chem. Soc. 1972, 94, 8205.
36. (b) Altona, C.; Sundaralingam, M. J. Am. Chem. Soc. 1973, 95, 2333.
37. (c) Haasnoot, C. A. G.; de Leeuw, F. A. A. M.; Altona, C. Tetrahedron 1980, 36, 2783.
38. Altona, C.; Ippel, J. H.; Aldert, J. A.; Hoekzema, W.; Erkelens, C.; Groesbeek, M.; Donders, L. A. Magn. Reson. Chem. 1989, 27, 564.