Intramolecular heck cyclisation-β-alkoxy elimination in carbohydrate chemistry. A simple route to to enantiopure annelated dioxatricyclic compounds

Synlett

Volumn , Issue 6, 1999, Pages 762-764

  Bedjeguelal, Karim ^a   Bolitt, Véronique ^a   Sinou, Denis ^a  

^a UNIVERSITÉ LYON 1   (France)

Author keywords

Carbohydrates; Cyclisation; Enantiopure heterocycles; Palladium

Indexed keywords

CARBOHYDRATE; HETEROCYCLIC COMPOUND; PALLADIUM; PYRANOSIDE;

ARTICLE; CARBOHYDRATE ANALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; ENANTIOMER; MOLECULAR INTERACTION; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0032997494     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2717     Document Type: Article

References (15)

1. Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38. Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, p 46. Grigg, R. J. Heterocycl. Chem. 1994, 31, 631. De Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. Thebtaranonth, C.; Thebtaranonth, Y. In Cyclisation Reactions; CRC Press: London, 1994; p 255. Tietze, L. F. Chem. Ind. (London) 1995, 453. Heumann, A.; Reglier, M. Tetrahedron 1995, 51, 975. Heumann, A.; Reglier, M. Tetrahedron 1996, 52, 9289. Negishi, E.; Coperet, C.; Ma, S.; Liou, S. Y.; Lin, F. Chem. Rev. 1996, 96, 365. Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
2. Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38. Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, p 46. Grigg, R. J. Heterocycl. Chem. 1994, 31, 631. De Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. Thebtaranonth, C.; Thebtaranonth, Y. In Cyclisation Reactions; CRC Press: London, 1994; p 255. Tietze, L. F. Chem. Ind. (London) 1995, 453. Heumann, A.; Reglier, M. Tetrahedron 1995, 51, 975. Heumann, A.; Reglier, M. Tetrahedron 1996, 52, 9289. Negishi, E.; Coperet, C.; Ma, S.; Liou, S. Y.; Lin, F. Chem. Rev. 1996, 96, 365. Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
3. Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38. Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, p 46. Grigg, R. J. Heterocycl. Chem. 1994, 31, 631. De Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. Thebtaranonth, C.; Thebtaranonth, Y. In Cyclisation Reactions; CRC Press: London, 1994; p 255. Tietze, L. F. Chem. Ind. (London) 1995, 453. Heumann, A.; Reglier, M. Tetrahedron 1995, 51, 975. Heumann, A.; Reglier, M. Tetrahedron 1996, 52, 9289. Negishi, E.; Coperet, C.; Ma, S.; Liou, S. Y.; Lin, F. Chem. Rev. 1996, 96, 365. Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
4. Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38. Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, p 46. Grigg, R. J. Heterocycl. Chem. 1994, 31, 631. De Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. Thebtaranonth, C.; Thebtaranonth, Y. In Cyclisation Reactions; CRC Press: London, 1994; p 255. Tietze, L. F. Chem. Ind. (London) 1995, 453. Heumann, A.; Reglier, M. Tetrahedron 1995, 51, 975. Heumann, A.; Reglier, M. Tetrahedron 1996, 52, 9289. Negishi, E.; Coperet, C.; Ma, S.; Liou, S. Y.; Lin, F. Chem. Rev. 1996, 96, 365. Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
5. Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38. Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, p 46. Grigg, R. J. Heterocycl. Chem. 1994, 31, 631. De Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. Thebtaranonth, C.; Thebtaranonth, Y. In Cyclisation Reactions; CRC Press: London, 1994; p 255. Tietze, L. F. Chem. Ind. (London) 1995, 453. Heumann, A.; Reglier, M. Tetrahedron 1995, 51, 975. Heumann, A.; Reglier, M. Tetrahedron 1996, 52, 9289. Negishi, E.; Coperet, C.; Ma, S.; Liou, S. Y.; Lin, F. Chem. Rev. 1996, 96, 365. Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
6. Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38. Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, p 46. Grigg, R. J. Heterocycl. Chem. 1994, 31, 631. De Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. Thebtaranonth, C.; Thebtaranonth, Y. In Cyclisation Reactions; CRC Press: London, 1994; p 255. Tietze, L. F. Chem. Ind. (London) 1995, 453. Heumann, A.; Reglier, M. Tetrahedron 1995, 51, 975. Heumann, A.; Reglier, M. Tetrahedron 1996, 52, 9289. Negishi, E.; Coperet, C.; Ma, S.; Liou, S. Y.; Lin, F. Chem. Rev. 1996, 96, 365. Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
7. Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38. Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, p 46. Grigg, R. J. Heterocycl. Chem. 1994, 31, 631. De Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. Thebtaranonth, C.; Thebtaranonth, Y. In Cyclisation Reactions; CRC Press: London, 1994; p 255. Tietze, L. F. Chem. Ind. (London) 1995, 453. Heumann, A.; Reglier, M. Tetrahedron 1995, 51, 975. Heumann, A.; Reglier, M. Tetrahedron 1996, 52, 9289. Negishi, E.; Coperet, C.; Ma, S.; Liou, S. Y.; Lin, F. Chem. Rev. 1996, 96, 365. Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
8. Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38. Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, p 46. Grigg, R. J. Heterocycl. Chem. 1994, 31, 631. De Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. Thebtaranonth, C.; Thebtaranonth, Y. In Cyclisation Reactions; CRC Press: London, 1994; p 255. Tietze, L. F. Chem. Ind. (London) 1995, 453. Heumann, A.; Reglier, M. Tetrahedron 1995, 51, 975. Heumann, A.; Reglier, M. Tetrahedron 1996, 52, 9289. Negishi, E.; Coperet, C.; Ma, S.; Liou, S. Y.; Lin, F. Chem. Rev. 1996, 96, 365. Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
9. Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38. Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, p 46. Grigg, R. J. Heterocycl. Chem. 1994, 31, 631. De Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. Thebtaranonth, C.; Thebtaranonth, Y. In Cyclisation Reactions; CRC Press: London, 1994; p 255. Tietze, L. F. Chem. Ind. (London) 1995, 453. Heumann, A.; Reglier, M. Tetrahedron 1995, 51, 975. Heumann, A.; Reglier, M. Tetrahedron 1996, 52, 9289. Negishi, E.; Coperet, C.; Ma, S.; Liou, S. Y.; Lin, F. Chem. Rev. 1996, 96, 365. Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
10. Oppolzer, W. Angew. Chem., Int. Ed. Engl. 1989, 28, 38. Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, p 46. Grigg, R. J. Heterocycl. Chem. 1994, 31, 631. De Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. Thebtaranonth, C.; Thebtaranonth, Y. In Cyclisation Reactions; CRC Press: London, 1994; p 255. Tietze, L. F. Chem. Ind. (London) 1995, 453. Heumann, A.; Reglier, M. Tetrahedron 1995, 51, 975. Heumann, A.; Reglier, M. Tetrahedron 1996, 52, 9289. Negishi, E.; Coperet, C.; Ma, S.; Liou, S. Y.; Lin, F. Chem. Rev. 1996, 96, 365. Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635.
11. Nguefack, J. F.; Bolitt, V.; Sinou, D. J. Org. Chem. 1997, 62, 1341 and 6827.
12. Grynkiewicz, G. Carbohydr, Res. 1984, 128, C9.
13. Clark, F. R. S.; Norman, R. O. C.; Thomas, B. C. J. Chem. Soc., Perkin Trans. 1 1975, 121.
14. Bedjeguelal, K.; Joseph, L.; Bolitt, V.; Sinou, D. Tetrahedron Lett. 1999, 40, 87.
15. 3) δ -5.4, -5.3, 18.4, 26.0, 34.1, 61.3, 68.3, 68.4, 76.6, 104.1, 124.2, 126.4, 127.1, 128.8, 134.2, 135.9, 141.9.