Stereoselective transformations on D-glucose-derived eight-membered ring carbocycles

Organic Letters

Volumn 3, Issue 5, 2001, Pages 731-733

  Van Hooft, Peter A V ^a   Litjens, Remy E J N ^a   Van Der Marel, Gijsbert A ^a   Van Boeckel, Constant A A ^b   Van Boom, Jacques H ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

^b NV ORGANON   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000988662     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol007047+     Document Type: Article

References (28)

1. Van Hooft, P. A. V.; Van der Marel, G. A.; Van Boeckel, C. A. A.; Van Boom, J. H. Tetrahedron Lett., in press.
2. Philippo, C. M. G.; Vo, N. H.; Paquette, L. A. J. Am. Chem. Soc. 1991, 113, 2762.
3. (b) Friedrich, D.; Paquette, L. A. J. Org. Chem. 1991, 56, 3831.
4. (c) Paquette, L. A.; Friedrich, D.; Rogers, R. D. J. Org. Chem. 1991, 56, 3841.
5. Das, S. K.; Mallet, J.-M.; Sinaÿ, P. Angew. Chem., Int. Ed. Engl. 1997, 36, 493.
6. (b) Sollogoub, M.; Mallet, J.-M.; Sinaÿ, P. Ang. Chem., Int. Ed. 2000, 39, 362.
7. (c) Sollogoub, M.; Pearce, A. J.; Hérault, A.; Sinaÿ, P. Tetrahedron: Asymmetry 2000, 11, 283.
8. For a review on the Baeyer-Villiger oxidation, see: Krow, G. R. In Organic Reactions, Volume 43; Paquette, L. A., Ed.; Wiley: New York, 1993.
9. Martin, O. R.; Szarek, W. A. Carbohydrate Res. 1984, 130, 195.
10. (b) Brimble, M.; Nairn, M. R.; Park, J. S. O. J. Chem. Soc., Perkin Trans. 1 2000, 5, 697.
11. For a review on the preparation of αβ-unsaturated ketones, see: Reich, J.; Wollowitz, S. In Organic Reactions, Volume 44; Paquette, L. A., Ed.; Wiley: New York, 1993.
12. Liotta, D.; Barnum, C.; Puleo, R.; Zima, G.; Bayer, C.; Kezar, H. S. J. Org. Chem. 1981, 46, 2920.
13. (b) Baker, R.; Gibson, C. L.; Swain, C. J.; Tapolczay, D. J. J. Chem. Soc., Perkin Trans. 1 1985, 1509.
14. Vedejs, E.; Wittenberger, S. J. J. Am. Chem. Soc. 1990, 112, 4357.
15. Gemal, A. L.; Luche, J.-L. J. Am. Chem. Soc. 1981, 103, 5454.
16. Overman, L. E. J. Am. Chem. Soc. 1976, 98, 2901.
17. Nishikawa, T.; Asai, M.; Ohyabu, N.; Isobe, M. J. Org. Chem. 1998, 63, 188.
18. Nicolaou, K. C.; Zhong, Y.-L.; Baran, P. S. Angew. Chem., Int. Ed. 2000, 39, 625.
19. (b) Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Vega, J. A. Angew. Chem., Int. Ed. 2000, 39, 2525.
20. For the first preparation of IBX, see: Hartman, C.; Meyer, V. Chem. Ber. 1893, 26, 1727. For a superior route to IBX, see: Frigerio, M.; Santagostino, M.; Sputore, S. J. Org. Chem. 1999, 64, 4537.
21. For the first preparation of IBX, see: Hartman, C.; Meyer, V. Chem. Ber. 1893, 26, 1727. For a superior route to IBX, see: Frigerio, M.; Santagostino, M.; Sputore, S. J. Org. Chem. 1999, 64, 4537.
22. Tepfer, D.; Goldmann, A.; Pamboukdjian, N.; Maille, M.; Lepingle, A.; Chevalier, D.; Denarie, J.; Rosenberg, C. J. Bacteriol. 1988, 170, 1153.
23. Asano, N.; Kato, A.; Matsui, K.; Watson, A. A.; Nash, R. J.; Molyneux, R. J.; Hackett, L.; Topping, J.; Winchester, B. Glycobiology 1997, 7, 1085.
24. Asano, N.; Nash, R. J.; Moyneux, R. J.; Fleet, G. W. J. Tetrahedron: Asymmetry 2000, 1645.
25. For representative examples on the preparation of carbocydic eight-membered rings, see: (a) Zora, M.; Koyuncu, I.; Yucel, B. Tetrahedron Lett. 2000, 41, 7111.
26. (b) Molander. G. A.; Machrouchi, F. J. Org. Chem. 1999, 64, 4119.
27. (c) Wender, P. A.; Nuss, J. M.: Smith, D. B.: Suarez-Sobrino, A.; Vagberg, J.; Decosta, D.; Bordner, J. J. Org. Chem. 1997, 62, 4908.
28. (d) Petasis, N. A.; Patane, M. A. Tetrahedron 1992, 48, 5757.