A novel carbocyclic ring closure of hex-5-enopyranosides and pent-4- enofuranosides

Synlett

Volumn , Issue 8, 1999, Pages 1289-1291

  Gallos, John K ^a   Koftis, Theocharis V ^a   Koumbis, Alexandras E ^a   Moutsos, Vassilios I ^a  

^a ARISTOTLE UNIVERSITY OF THESSALONIKI   (Greece)

Author keywords

Carbocycles; Carbohydrates; Enaminones; Hydrogenation; Nitrile oxides

Indexed keywords

CARBOHYDRATE DERIVATIVE; CYCLOHEXANE; CYCLOPENTANE; HETEROCYCLIC COMPOUND; HEX 5 ENOPYRANOSIDE; ISOXAZOLINE DERIVATIVE; NITRILE; PENT 4 ENOFURANOSIDE; SPIROISOXAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBOHYDRATE SYNTHESIS; COLUMN CHROMATOGRAPHY; HYDROGENATION; HYDROLYSIS; POLYMERIZATION;

EID: 0032792532     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2792     Document Type: Article

References (28)

1. Fraser-Reid, B. Acc. Chem. Res. 1996, 29, 57.
2. (a) Ferrier, R. J.; Middleton, S. Chem. Rev. 1993, 93, 2779.
3. (b) Berecibar, A.; Grandjean, C.; Siriwardena, A. Chem. Rev. 1999, 99, 779.
4. (a) Chretien, F.; Khaldi, M.; Chapleur, Y. Tetrahedron Lett. 1997, 38, 5977.
5. (b) Cere, V.; Peri, F.; Pollicino, S. Tetrahedron Lett. 1997, 38, 7797.
6. Gothelf, K. V.; Jorgensen, K. A. Chem. Rev. 1998, 98, 863.
7. (a) Martinez-Grau, A.; Marco-Contelles, J. Chem. Soc. Rev. 1998, 27, 155.
8. (b) Marco-Contelles, J.; Alhambra, C.; Martinez-Grau, A. Synlett 1998, 693.
9. Selected recently published papers: (a) Ito, H.; Motoki, Y.; Taguchi, T.; Hanzawa, Y. J. Am. Chem. Soc. 1993, 115, 8835.
10. (b) Mukai, C.; Uchiyama, M.; Sakamoto, S.; Hanaoka, M. Tetrahedron Lett. 1995, 36, 5761.
11. (c)Iimori, T.; Takahashi, H.; Ikegami, S. Tetrahedron Lett. 1996, 37, 649.
12. (d.)Das, S. K.; Mallet, J.-M.; Sinay, P. Angew. Chem. Int. Ed. Engl. 1997, 36, 493.
13. (e) Sollogoub, M.; Mallet, J.-M.; Sinay, P. Tetrahedron Lett. 1998, 39, 3471.
14. (a) Ovaa, H.; Codee, J. D. C.; Lastdrager, B.; Overleeft, H. S.; van der Marel, G. A., van Boom, J. H. Tetrahedron Lett. 1998, 39, 3025.
15. (b) Sellier, O.; Van de Weghe, P.; Le Nouen, D.; Strehler, C.; Eustache, J. Tetrahedron Lett. 1999, 40, 853.
16. (a) Gallos, J. K.; Koftis, T. V.; Koumbis, A. E. J. Chem. Soc., Perkin Trans. 1, 1994, 611.
17. (b) Ohira, S.; Sawamoto, T.; Yamato, M. Tetrahedron Lett. 1995, 36, 1537.
18. (c)Sudha, A. V. R. L.; Nagarajan, M. Chem. Commun., 1998, 925.
19. Ferrier, R. J. J. Chem. Soc., Perkin Trans. I 1979, 1455.
20. (a) Gallos, J. K.; Koumbis, A. E.; Apostolakis, N.E. J. Chem. Soc., Perkin Trans. I 1997, 2457.
21. (b) Gallos, J. K.; Koftis, T.V.; Karamitrou, V. I.; Koumbis, A. E. J. Chem. Soc., Perkin Trans. I 1997, 2461.
22. Curran, D. P. Adv. Cycloaddition 1988, 1, 129.
23. Hill, J. M.; Hutchinson, E. J.; Le Grand, D. M.; Roberts, S. M., Thorpe, A. J.; Turner, N. J. J. Chem. Soc., Perkin Trans. I 1994, 1483.
24. 3) 28.24, 71.65, 73.77, 74.21, 78.52, 84.12, 99.00, 127.41, 127.49, 127.57, 127.92, 128.07, 128.20, 128.26, 128.49, 130.82, 133.37, 134.05, 138.47, 138.52, 138.55, 155.32 and 195.99.
25. Boa, A. N.; Booth, S. E.; Dawkins, D. A.; Jenkins, P. R.; Fawcett, J.; Russell, D. R. . J. Chem, Soc., Perkin Trans. 1 1993, 1277.
26. (a) Mukaiyama, T.; Hoshino, T. J. Am. Chem. Soc. 1960, 82, 5339,
27. (b) Hassner, A.; Dehaen, W. J. Org. Chem. 1990, 55, 5505.
28. Zhuo, J.-C. Magn. Res. Chem. 1998, 36, 565.