Ring-closing metathesis in carbohydrate annulation

Angewandte Chemie - International Edition

Volumn 37, Issue 23, 1998, Pages 3298-3300

  Holt, David J ^a   Barker, William D ^a   Jenkins, Paul R ^a   Davies, David L ^a   Garratt, Shaun ^a   Fawcett, John ^a   Russell, David R ^a   Ghosh, Subtrata ^b  

^a UNIVERSITY OF LEICESTER   (United Kingdom)

^b DEPARTMENT OF MATERIALS SCIENCE   (India)

Author keywords

Annulation; Carbohydrates; Homogeneous catalysis; Metathesis; Ruthenium

Indexed keywords

CARBOHYDRATE DERIVATIVE; RUTHENIUM;

ARTICLE; CARBOHYDRATE METABOLISM; CATALYST; CHIRALITY; CRYSTAL STRUCTURE; CYCLIZATION; ORGANIC CHEMISTRY; X RAY ANALYSIS;

EID: 0032542279     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19981217)37:23<3298::AID-ANIE3298>3.0.CO;2-O     Document Type: Article

References (45)

1. S. Hanessian, Total Synthesis of Natural Products; The Chiron Approach, Pergamon, Oxford, 1993.
2. R. J. Ferrier, S. Middleton, Chem. Rev. 1993, 93, 2779;
3. J. C. Lopez, B. Fraser-Reid, Chem. Commun. 1997, 2251.
4. [31 R. V. Bonnert. P. R. Jenkins. J. Chem. Soc. Chem. Commun. 1987, 6;
5. R. V. Bonnert, J. Howarth, P. R. Jenkins, N. J. Lawrence, J. Chem. Soc. Perkin Trans, 1 1991, 1225.
6. A. J. Wood, P. R. Jenkins, J. Fawcett, D. R. Russell, J. Chem. Soc. Chem. Commun. 1995, 1567.
7. R. V. Bonnert, M.J. Davies, J. Howarth, P. R. Jenkins, J. Chem. Soc. Chem. Commun. 1987, 148;
8. R. V. Bonnert, M. J. Davies, J. Howarth, P. R. Jenkins, N. J. Lawrence, J. Chem. Soc. Perkin Trans. 1 1992, 27;
9. A. J. Wood, P. R. Jenkins, Tetrahedron Lett., 1997, 38, 1853.
10. A. N. Boa, J. Clark, P. R. Jenkins, N. J. Lawrence, J. Chem. Soc. Chem. Commun. 1993, 151.
11. A. Fürstner, Top. Catal. 1997, 4, 285;
12. S. Blechert, M. Schuster, Angew: Chem. 1997, 109, 2124;
13. Angew: Chem. Int. Ed. Engl. 1997, 36, 2036;
14. R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413;
15. S. K. Armstrong, J. Chem. Soc. Perkin Trans 1 1998, 371.
16. P. Schwab, M. B. France, J. W. Ziller, R. H. Grubbs, Angew: Chem. 1995, 107, 2179;
17. Angew. Chem. Int. Ed. Engl. 1995, 34, 2039;
18. P. Schwab, R. H. Grubbs, J. Am. Chem. Soc. 1996, 118, 100.
19. H. S. Overkleeft, U. K. Pandit, Tetrahedron Lett. 1996, 37, 547;
20. M. A. Leeuwenburgh, H. S. Overkleeft, G. A. van der Marel, J. H. van-Boom, Synlett 1997, 1263;
21. H. Ovaa, M. A. Leeuwenburgh, H. S. Overkleeft, G. A. van der Marel, J. H. van Boom, Tetrahedron Lett. 1998, 39, 3025;
22. H. S. Overkleeft, P. Bruggeman, U.K. Pandit, Tetrahedron Lett. 1988, 39, 3869.
23. G. Descotes, J. Ramza, J.-M. Basset, S. Pagano, E. Gentil, J. Banoub, Tetrahedron 1996, 52, 10903.
24. H. E. Sukkari, J.-P. Gesson, B. Renoux, Tetrahedron Lett. 1998, 39, 4043.
25. A. Fürstner, T. Muller, J. Org. Chem. 1998, 63, 424.
26. F. E. Ziegler, Y. Wang, J. Org. Chem. 1998, 63, 426.
27. P. R. Jenkins, Pure Appl. Chem. 1996, 68, 771.
28. R. J. Ferrier, C.-K. Lee, T. A. Wood, J. Chem. Soc. Chem Commun. 1991, 690.
29. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-101536, 101537, 101538, 101539, and 1015340. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK deposit@ccdc.cam.ac.uk
30. B. Werschkun, J. Thiem, Angew. Chem. 1997, 109, 2905;
31. Angew. Chem. Int. Ed. Engl. 1997, 36, 2793.
32. a) S. J. Miller, S.-H. Kim, Z.-R. Chen, R. H. Grubbs, J. Am. Chem. Soc. 1995, 117, 2108;
33. b) M. S. Visser, N. M. Heron, M. T. Didiuk, J. F. Sagal, A. H. Hoveyda, J. Am. Chem. Soc. 1996, 118, 4291;
34. c) A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 8746;
35. d) J. S. Clark, J. G. Kettle, Tetrahedron Lett. 1997, 38, 123; 127.
36. Studies are underway aimed at improving these poor yields.
37. a) D. D. Reynolds, W. O. Kenyon, J. Am. Chem. Soc. 1950, 72, 1593;
38. P. Picard, D. Leclercq, J. Moulines, Tetrahedron Lett. 1975, 2731;
39. P. Canonne, G. B. Foscolos, D. Belanger, J. Org. Chem. 1980, 45, 1828;
40. E. Piers, V. G. Ashvinikumar, J. Org. Chem. 1990, 55, 2380;
41. b) D. S. Middleton, N. S. Simpkins, Tetrahedron Lett. 1988, 29, 1315;
42. c) L. A. Paquette, J. Tae, J. Org. Chem. 1996, 61, 7860;
43. d) L. A. Paquette, J. T. Negri, J. Am. Chem. Soc. 1991, 113, 5072.
44. After submission of this paper a publication appeared on the spiroannulation of a different set of sugar derivatives by RCM: P. A. V. van Hooft, M. A. Leeuvwenburgh, H. S. Overkleeft, G. A. vender Marel, C.A. A. van Boeckel, J. H. van Boom, Tetrahedron Lett. 1998, 39, 6061
45. A. Rosenthal, P. Catsoulacos, Can. J. Chem. 1969, 47, 2747.