An Efficient Way to 1,7-Enynes and Ethyl 8-Yn-2-enoates from Aldohexoses and to Polyhydroxylated 1-Vinylcyclohexenes

Journal of Organic Chemistry

Volumn 69, Issue 10, 2004, Pages 3400-3407

  Dolhem, Franck ^a   Lièvre, Catherine ^a   Demailly, Gilles ^a  

^a UNIVERSITÉ DE PICARDIE JULES VERNE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; DERIVATIVES; SYNTHESIS (CHEMICAL);

1,7-ENYNES; METALTHESIS; MORI'S CONDITIONS; POLYHYDROXYLATED 1-VINYLCYCLOHEXENES;

CARBOHYDRATES;

1 VINYLCYCLOHEXENE; 1,7 ENYNE; 6,7 DIDEOXY DEXTRO GLUCOHEPT 6 ENE PYRANOSE; ALKENE; CARBOHYDRATE; CYCLOHEXENE DERIVATIVE; ETHYL 8 YN 2 ENOATE; GLUCOSE; MONOSACCHARIDE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CYCLIZATION; HYDROXYLATION; INFRARED SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 2442429394     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035437e     Document Type: Article

References (28)

1. (a) Hanessian, S. Total Synthesis of Natural Products: The "Chiron" Approach; Pergamon Press: Oxford, 1933.
2. (b) Rollin, P.; Klaffke, W. J. Carbohydr. Chem. 1991, 10, 115.
3. Lièvre, C. Dissertation, Université d'Amiens, 1996.
4. (a) Lièvre, C.; Fréchou, C.; Demailly, G. Tetrahedron Lett. 1995, 36, 6467.
5. (b) Le Mignot, V.; Lièvre, C.; Fréchou, C.; Demailly, G. Tetrahedron Lett. 1998, 39, 983.
6. (c) Lièvre, C.; Fréchou, C.; Demailly, G. Carbohydr. Res. 1997, 303, 1.
7. Dolhem, F.; Lièvre, C.; Demailly, G. Tetrahedron Lett. 2002, 43, 1847.
8. Dolhem, F. Dissertation, Urdversité d'Amiens, 2003.
9. Thiéry, J.-C. Dissertation, Université d'Amiens, 2000.
10. Thiéry, J.-C.; Fréchou, C.; Demailly, G. Tetrahedron Lett. 2000, 41, 6337.
11. Dolhem, F.; Lièvre, C.; Demailly, G. Tetrahedron 2003, 59, 155.
12. (a) Ferrier, R. R.; Middleton, S. Chem. Rev. 1993, 93, 2279.
13. (b) Collins, P.; Ferrier, R. R. Monosaccharides; Wiley: Chichester, 1995.
14. Dolhem, F.; Lièvre, C.; Demailly, G. Eur. J. Org. Chem. 2003, 2336.
15. Mori, M.; Sakakira, N.; Kinoshita, A. J. Org. Chem. 1998, 63 (18), 6082.
16. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1 (6), 953.
17. (a) Kapferer, P.; Sarabia, F.; Vasella, A. Helv. Chim. Acta 1999, 82, 645.
18. (b) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012.
19. (c) Marco-Contelles, J.; de Opazo, E. J. Org. Chem. 2002, 67, 3705.
20. (d) Storm-Paulsen, C.; Madsen, R. Synthesis 2003, 1, 1.
21. Muzart, J. Synthesis 1993, 11.
22. Rodriguez, A.; Nomen, M.; Spur, B. W.; Godfroid, J. J. Tetrahedron Lett. 1999, 40, 5161.
23. Nicotra, F.; Ronchetti, F.; Russo, G.; Toma, L. Tetrahedron Lett. 1984, 49, 5697.
24. Kolb, M.; Witz, P.; van Hijfte, L. Tetrahedron Lett. 1989, 30, 3769.
25. Corey, E. J.; Fuchs. P. L. Tetrahedron Lett. 1972, 36, 3769.
26. Gennet, D.; Michel, P.; Rassat, A. Tetrahedron Lett. 1999, 40, 8575.
27. (a) Kitamura, T.; Sato, Y.; Mori, M. J. Chem. Soc., Chem. Commun. 2001, 1258.
28. (b) Kitamura, T.; Sato, Y.; Mori, M. Adv. Synth. Catal. 2002, 344, 678.