Indium-mediated Reformatsky reaction on lactones: preparation of 2-deoxy-2,2′-dimethyl-3-ulosonic acids

Tetrahedron Letters

Volumn 51, Issue 1, 2010, Pages 105-108

  Soengas, Raquel G ^a  

^a UNIVERSITY OF A CORUÑA   (Spain)

Author keywords

Indium; Reformatsky reaction; Sugar lactones; Ulosonic acids

Indexed keywords

LACTONE; SUGAR;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; REFORMATSKY REACTION; SYNTHESIS; ULTRASOUND;

EID: 70649097079     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.10.092     Document Type: Article

References (38)

1. Watterson M.P., Edwards A.A., Leach J.A., Smith M.D., Ichihara O., and Fleet G.W.J. Tetrahedron Lett. 44 (2003) 5853-5857
2. Asano N., Nash R.J., Molyneux R.J., and Fleet G.W.J. Tetrahedron: Asymmetry 11 (2000) 1645-1680
3. Long D.D., Smith M.D., Martin A., Wheatley J.R., Watkin D.G., Muller M., and Fleet G.W.J. J. Chem. Soc., Perkin Trans. 1 (2002) 1982-1998
4. Csuk R., and Glänzer B.I. J. Carbohydr. Chem. 9 (1990) 797-807
5. Grassberger V., Berger A., Dax K., Fechter M., Gradnig G., and Stütz A.E. Liebigs Ann. Chem. (1993) 379-390
6. Hanessian S., and Giraud C. Synlett (1994) 865-867
7. Orsini F., and di Teodoro E. Tetrahedron: Asymmetry 14 (2003) 2521-2528
8. Csuk R., Franke U., Hu Z., and Krieger C. Tetrahedron 59 (2003) 7887-7895
9. Cuenca A.B., D'Hooge F., Gouge V., Castelot-Deliencourt G., Oulyadi H., Leclerc E., Jubault P., Pannecoucke X., and Quirion J.-C. Synlett 17 (2005) 2627-2630
10. Araki S., Ito H., Katsumura N., and Butsugan Y. J. Organomet. Chem. 369 (1989) 291-296
11. Cintas P. Synlett (1995) 1087-1096
12. Podlech J., and Maier T.C. Synthesis (2003) 633
13. Nair V., Ros R., Jayan C.N., and Pillai B. Tetrahedron 60 (2004) 1959-1982
14. Babu S.A., Yasuda M., Shibata I., and Baba A. J. Org. Chem. 70 (2005) 10408-10419
15. Kim E., Gordon D.M., Schmid W., and Whitesides G.M. J. Org. Chem. 58 (1993) 5500-5507
16. Chan T.H., and Isaac M.B. Pure Appl. Chem. 68 (1996) 919-924
17. Canac Y., Levoirier E., and Lubineau A. J. Org. Chem. 66 (2001) 3206-3210
18. Levoirier E., Canac Y., Norsikian S., and Lubineau A. Carbohydr. Res. 339 (2004) 2737-2747
19. Balla E., Zamyatina A., Hofinger A., and Kosma P. Carbohydr. Res. 342 (2007) 2537-2545
20. Alcaide B., Almendros P., and Rodríguez-Acebes R. J. Org. Chem. 67 (2002) 1925-1928
21. Chan t., Hang L., and Chao J. J. Chem. Soc., Chem. Commun. (1992) 747-748
22. +) calculated 239.1253. Found: 239.1250.
23. 3 to the lactone. Tussa L., Lebreton C., and Mosset P. Chem Eur. J. 3 (1997) 1064-1070
24. Pommier A., and Pons J.-M. Synthesis (1993) 441-459
25. Luzzio F.A. The Oxidation of Alcohols by Modified Oxochromium(IV)-Amine Reagents, Organic Reactions Vol. 53 (1998), Hoboken, N.J., United States
26. Bayshal B.P., Hak Fun C., Fellows L.E., and Fleet G.W.J. Tetrahedron 43 (1987) 415-422
27. Banda, G.; Chakravarthy, I. E. Tetrahedron: Asymm. 2006, 17, 1684-1687.
28. Lefeber D.J., Steunenberg P., Vliengenthart J.F.G., and Kamerling J.P. Tetrahedron: Asymmetry 16 (2005) 507-511
29. Obtained from selective deprotection of the primary hydroxyl group by treatment with PPTS in EtOH at 50 °C of the corresponding 5-O-(1-methoxy-1-methyl-ethoxymetyl) derivative, prepared as described in the literature:. Hanessian S., Stephane M., Machaalani R., Huang G., Pierron J., and Loiseleur O. Tetrahedron 62 (2006) 5201-5214
30. Chiara J.L., Cabri W., and Hanessian S. Tetrahedron. Lett. 32 (1991) 1125-1128
31. Hanessian S., Girard C., and Chiara J.L. Tetrahedron. Lett. 33 (1992) 573-576
32. Girard C., and Hanessian S. Synlett (1994) 861-862
33. Girard C., and Hanessian S. Synlett (1994) 863-864
34. 3 in C-2 and between H-4/H-5 and the ethyl group.{A figure is presented}
35. 3 in C-2 and between H-4 and the ethyl group.{A figure is presented}
36. Ogura H., Hosegawa A., and Suami T. Carbohydrates, Synthetic Methods and Applications in Medicinal Chemistry (1992), VCH, Cambridge, Basel
37. Unger F.M. Adv. Carbohydr. Chem. Biochem. 38 (1981) 323-388
38. Schauer R. Adv. Carbohydr. Chem. Biochem. 40 (1982) 131-234