Claisen-Ireland rearrangement: A new route to C-glycosides

Tetrahedron Letters

Volumn 40, Issue 31, 1999, Pages 5677-5680

  Vidal, Thierry ^a   Haudrechy, Arnaud ^a   Langlois, Yves ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

GALACTOSAMINE; GLUCOSAMINE DERIVATIVE; GLYCAN DERIVATIVE; GLYCOSIDE; LACTONE;

ARTICLE; CHIRALITY; HYDROXYLATION; IONIZATION; NITRATION; REACTION ANALYSIS; REDUCTION; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

EID: 0033618291     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01055-2     Document Type: Article

References (22)

1. For recent reviews, see: (a) Simanek, E. E.; Mc Gravey, G. J.; Jablonowski, J. A.; Wong, C.-H. Chem. Rev. 1998, 98, 833-862.
2. (b) Dwek, R. A. Chem. Rev. 1996, 96, 683-720.
3. (c) Lee, Y. C.; Lee, R. T. Acc. Chem. Res. 1995, 28, 321-327.
4. (a) Dondoni, A.; Marra, A.; Massi, A. J. Org. Chem. 1999, 64, 933-944, and references cited therein.
5. (b) Levy, D. E.; Tang, C. The Chemistry of C-Glycosides; Pergamon: Oxford, 1995.
6. (a) Curran, D. P.; Suh, Y. G. Carbohydr. Res. 1987, 171, 161-191.
7. (b) Colombo, L.; Casigari, G.; Pittalis, A.; Rassu, G. J. Org. Chem. 1991, 56, 3897-3900.
8. Compound 5 was prepared from D-(+)-galactose in 38% overall yield for six steps according to: Bröder, W.; Kuntz, H. Carbohydr. Res. 1993, 249, 221-241.
9. (a) Pougny, J. R.; Nassr, M. A.; Sinaÿ, P. J. Chem. Soc., Chem. Comm. 1981, 375-376.
10. (b) Liu, P. S. J. Org. Chem. 1987, 52, 4717-4721.
11. (c) Qiao, L.; Vederas, J. C. J. Org. Chem. 1993, 58, 3480-3482.
12. (a) Nicotra, F.; Perego, R.; Ronchetti, F.; Russo, G.; Toma, L. Gazz. Chim. Ital. 1984, 114, 193-195.
13. (b) Boshetti, A.; Nicotra, F.; Panza, L.; Rosso, G. J. Org. Chem. 1988, 53, 4181-4185.
14. (c) Casero, F.; Cipolla, L.; Lay, L.; Nicotra, F.; Panza, L.; Russo, G. J. Org. Chem. 1996, 61, 3428-3432.
15. Martin, O. R.; Xie, F. Carbohydr. Res. 1994, 264, 141-146.
16. For a recent review concerning the asymmetric Claisen rearrangement, see: Ito, T.; Taguchi, T. Chem. Soc. Rev. 1999, 28, 43-50.
17. 4 and evaporated in vacuo. The resulting acid derivative was treated without purification with an etheral solution of diazomethane affording the ester 11b (131 mg, 91%) as 64:36 mixture of diastereomers after purification by column chromatography (silica gel, heptane:AcOEt, 8:2).
18. Similar lithium coordination precluding ester deprotonation has been observed, see: Schow, S. R.; Bloom, J. D.; Thompson, A. S.; Winzenberg, K. N.; Smith III, A. B. J. Am. Chem. Soc. 1986, 108, 2662-2674.
19. Canet, I.; Meddour, A.; Loewenstein, A.; Péchiné, J.-M.; Courtieu, J. J. Am. Chem. Soc. 1995, 117, 6520-6526.
20. (a) Lemieux, R. U.; Ratcliffe, R. M. Can. J. Chem. 1979, 57, 1244-1251.
21. (b) For a review, see: Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E. Stereoselective Synthesis; G. Thieme Verlag: Stuttgart, 1996; Vol. 9, pp. 5208-5212.
22. Vedejs, E.; Bennett, N. S.; Conn, L. M.; Diver, S. T.; Gingras, M.; Lin, S.; Oliver, P. A.; Peterson, M. J. J. Org. Chem. 1993, 58, 7286-7288 and references cited therein.