Synthesis of carbohydrate-derived enynes and subsequent metathesis to yield polyhydroxylated 1-vinylcycloalkenes

European Journal of Organic Chemistry

Volumn , Issue 12, 2003, Pages 2336-2342

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

^a UNIVERSITÉ DE PICARDIE JULES VERNE   (France)

Author keywords

Carbohydrate derived enynes; Polyhydroxylated 1 vinylcyclohexenes; Polyhydroxylated 1 vinylcyclopentenes; Ring closing enyne metathesis reaction

Indexed keywords

1 O TRITYLHEPT 6 YNE 1,2,3,4 TETROL; 1 VINYLCYCLOPENTENE; 3,4,5 TRI O BENZYL 1 VINYLCYCLOHEXENE 3,4,5 TRIOL; 3,4,5 TRI O BENZYLHEPT 6 EN 1 YNE 3,4,5 TRIOL; 3,4,5,6 TETRA O BENZYLOCT 7 EN 1 YNE 3,4,5,6 TETROL; 4,5 DI O BENZYLHEPT 6 EN 1 YNE 4,5 DIOL; 4,5,6 TRI O BENZYLOCT 7 EN 1 YNE 4,5,6 TRIOL; ALKENE DERIVATIVE; CARBOHYDRATE; CARBOHYDRATE DERIVATIVE; CYCLOALKENE; GLYCO YNITOL; GLYCOSIDE; HETEROCYCLIC COMPOUND; MONOSACCHARIDE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL REACTION; CYCLIZATION; RING CLOSING METATHESIS; SYNTHESIS;

EID: 0038391513     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300102     Document Type: Article

References (20)

1. For a review on enyne cycloisomerization reactions, see: C. Aubert, O. Buisine, M. Malacria, Chem. Rev. 2002, 102, 813-834.
2. For review, see: C. S. Poulsen, R. Madsen, Synthesis 2003, 1-18.
3. J. C. Thièry, PhD Dissertation, Université de Picardie, 2000.
4. Carbohydrate Mimics, Concepts and Methods (Ed.: Y. Chapleur), Wiley-VCH, Weinheim, 1998.
5. C. S. Poulsen, R. Madsen, J. Org. Chem. 2002, 67, 4441-4449.
6. F. D. Boyer, I. Hanna, L. Ricard, Org. Lett. 2001, 3, 3095-3098.
7. J. Marco-Contelles, N. Arroyo, J. Ruiz-Caro, Synlett 2001, 652-655.
8. M. A. Leeuwenburgh, C. C. M. Appeldoorn, P. A. V. van Hooft, H. S. Overkleeft, G. A. van der Marel, J. H. van Boom, Eur. J. Org. Chem. 2000, 873-877.
9. M. A. Leeuwenburgh, C. Kulker, H. I. Duynstee, H. S. Overkleeft, G. A. van der Marel, J. H. van Boom, Tetrahedron 1999, 55, 8253-8262.
10. J. S. Clark, O. Hamelin, Angew. Chem. Int. Ed. 2000, 39, 372-374.
11. T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18-29.
12. A. Fürstner, Angew. Chem. Int. Ed. 2000, 39, 3012-3043.
13. R. R. Schrock, Tetrahedron 1999, 55, 8141-8153.
14. M. Jorgensen, P. Hadwiger, R. Madsen, A. E. Stütz, T. M. Wrodnigg, Curr. Org. Chem. 2000, 4, 565-588.
15. R. Roy, S. K. Das, Chem. Commun. 2000, 519-529.
16. F. Dolhem, C. Lièvre, G. Demailly, Tetrahedron Lett. 2002, 43, 1847-1849.
17. F. Dolhem, C. Lièvre, G. Demailly, Tetrahedron 2003, 59, 155-164.
18. M. Mori, N. Sakakira, A. Kinoshita, J. Org. Chem. 1998, 63, 6082-6083.
19. T. Kitamura, Y. Sato, M. Mori, Chem. Commun. 2001, 1258-1259.
20. M. Mori, N. Sakakira, A. Kinoshita, Adv. Synth. Catal. 2002, 334, 678-693.