Corrigendum to "Stereocontrolled synthesis of (5+5), (5+6) and (6+6) 3-spiropseudonucleosides" [Tetrahedron 65 (21) (2009) 4149-4155] (DOI:10.1016/j.tet.2009.03.038);Stereocontrolled synthesis of (5+5), (5+6) and (6+6) 3-spiropseudonucleosides

Tetrahedron

Volumn 65, Issue 21, 2009, Pages 4149-4155

  Gasch, Consolación ^a   Illangua, José M ^a   Merino Montiel, Penélope ^a   Fuentes, José ^a  

^a UNIVERSITY OF SEVILLE   (Spain)

Author keywords

Imidazolidine; Isothiocyanatosugar; Oxazolidine; Perhydrooxazine; Spironucleoside; Thiohydantoin

Indexed keywords

3 SPIROPSEUDONUCLEOSIDE; CARBOHYDRATE DERIVATIVE; IMIDAZOLINE DERIVATIVE; ISOTHIOCYANIC ACID; OXAZOLIDINE DERIVATIVE; PERHYDROOXAZINE; THIOHYDANTOIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 64649092600     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.01.076     Document Type: Erratum

References (46)

1. Fernández-Bolaños J., Blasco López A., and Fuentes Mota J. Carbohydr. Res. 199 (1990) 239-242
2. Gimisis T., Castellari C., and Chatgilialoglu Ch. Chem. Commun. (1997) 2089-2090
3. Renard A., Lhomme J., and Kotera M. J. Org. Chem. 67 (2002) 1302-1307
4. Sayago F.J., Pradera M.A., Gasch C., and Fuentes J. Tetrahedron 62 (2006) 915-921
5. See as examples:
6. Poland B.W., Lee S.F., Subramanian M.V., Siehl D.L., Andersen R.J., Fromm H.J., and Honzatko R.B. Biochemistry 35 (1996) 15753-15759
7. Fonne-Pfister R., Chemia P., Ward E., Girarded M., Krenz K.E., Honzatko R.B., Fromm H.J., Schar H.-P., Grütter M.G., and Cowan-Jacob S.W. Proc. Natl. Acad. Sci. U.S.A. 93 (1996) 9431-9436
8. Walters E.W., Lee S.F., Niderman T., Bernasconi P., Subramanian M.V., and Siehl D.L. Plant Physiol. 62 (1997) 125-134
9. Somsák L., Nagy V., Vidal S., Czifrák K., Berzsényi E., and PralyPoland J.-P. Bioorg. Med. Chem. Lett. 18 (2008) 5680-5683
10. Gyémánt G., Kandra L., Nagy V., and Somsák L. Biochem. Biophys. Res. Commun. 312 (2003) 334-339
11. Kapferer P., Birault V., Poisson J.-F., and Vasella A. Helv. Chim. Acta 86 (2003) 2210-2226
12. Mio S., Ichinose R., Goto K., Sugai S., and Sato S. Tetrahedron 47 (1991) 2111-2120
13. Mio S., Kumagawa Y., and Sugai S. Tetrahedron 47 (1991) 2133-2144
14. Matsumoto M., Kirihara M., Yoshino T., Katoh T., and Terashima S. Tetrahedron Lett. 34 (1993) 6289-6292
15. Chemla P. Tetrahedron Lett. 34 (1993) 7391-7394
16. Harrington P.M., and Jung M.E. Tetrahedron Lett. 35 (1994) 5145-5148
17. Nakajima N., Matsumoto M., Kirihara M., Hashimoto M., Katoh T., and Terashima S. Tetrahedron 52 (1996) 1177-1194
18. See as examples:
19. Fuentes J., Salameh B.A.B., Pradera M.A., Fernández de Córdoba F.J., and Gasch C. Tetrahedron 62 (2006) 97-111 and references cited therein
20. Long D.D., Smith M.D., Martín A., Wheatley J.R., Watkin D.G., Müller M., and Fleet G.W.J. J. Chem. Soc., Perkin Trans. 1 (2002) 1982-1998 For reviews see:
21. Schweizer F. Angew. Chem., Int. Ed. 41 (2002) 230-253
22. Dondoni A., and Marra A. Chem. Rev. 100 (2000) 4395-4421
23. Tardy S., Vicente J.L., Tatibouët A., Dujardin G., and Rollin P. Synthesis 19 (2008) 3108-3120
24. Bouifraden S., Lavergne J.P., Martinez J., Viallefont P., and Riche C. Tetrahedron: Asymmetry 8 (1997) 949-955
25. Postel D., Van Nhien A.N., Villa P., and Ronco G. Tetrahedron Lett. 42 (2001) 1499-1502
26. Van Nhien A.N., Ducatel H., Len C., and Postel D. Tetrahedron Lett. 43 (2002) 3805-3808
27. Shibata K., Hiruma K., Kanie O., and Wong C.-H. J. Org. Chem. 65 (2000) 2393-2398
28. Roy A., Achari B., and Mandal S.B. Tetrahedron Lett. 47 (2006) 3875-3879
29. De Castro S., Lobatón E., Pérez-Pérez M.J., San-Félix A., Cordeiro A., Andrei G., Snoeck R., De Clercq E., Balzarini J., Camarasa M.J., and Velázquez S. J. Med. Chem. 48 (2005) 1158-1168
30. López O., Zafra A., Maya I., Fuentes J., Diánez M.-J., Estrada M.-D., Pérez-Garrido S., and Fernández-Bolaños J.-G. Tetrahedron 64 (2008) 11789-11796 and references cited therein
31. Turconi J., Lebeau L., Paris J.-M., and Mioskowski C. Tetrahedron Lett. 47 (2006) 121-124
32. Crimmins M.T., Katz J.D., Washburn D.G., Allwein S.P., and McAtee L.F. J. Am. Chem. Soc. 124 (2002) 5661-5663
33. These results on the synthesis of 3-spiropseudonucleosides were communicated to the 6th Italian Sapanish Symposium on Organic Chemistry. Taormina, Italy, July 2006. See in book of abstracts Gasch, C.; Pradera, M. A.; Illangua, J. M.; Fuentes J., communication P020, p. 97.
34. For the preparation of sugar isothiocyanato derivatives see. Fuentes J., Illangua J.M., Sayago F.J., Angulo M., and Gasch C. Tetrahedron: Asymmetry 15 (2004) 3783-3789 and references cited therein. See also Ref. 6a
35. Saito Y., Zevaco T.A., and Agrofoglio L.A. Tetrahedron 58 (2002) 9593-9603
36. Van Nhien A.N., Domi{dotless}ínguez L., Tomassi C., Torres M.R., Len C., Postel D., and Marco-Contelles J. Tetrahedron 60 (2004) 4709-4723
37. This reaction was described by. Corey E.J., and Link J.O. J. Am. Chem. Soc. 114 (1992) 1906-1908 and takes place through an intermediate dichloroepoxide
38. A synthesis of 18 through a spiroepoxide has been recently reported. See Ref. 7a.
39. Fuentes J., Molina J.L., Olano D., and Pradera M.A. Tetrahedron: Asymmetry 7 (1996) 203-218
40. Marino C., Varela O., and Lederkremer R.H. Carbohydr. Res. 304 (1997) 257-260
41. De Mesmaeker A., Haener R., Martin P., and Moser H.E. Acc. Chem. Res. 28 (1995) 366-374
42. Katritzky A.R. Handbook of Heterocyclic Chemistry (1985), Pergamon, Oxford p 105
43. Gasch C., Pradera M.A., Salameh B.A.B., Molina J.L., and Fuentes J. Tetrahedron: Asymmetry 12 (2001) 1267-1277
44. López O., Maza S., Maya I., Fuentes J., and Fernández-Bolaños J.B. Tetrahedron 61 (2005) 9058-9069
45. Ávalos González M., Cintas Moreno P., Gómez Monterrey I.M., Jiménez Requejo J.L., Palacios Albarrán J.C., Rebolledo Vicente F., and Fuentes Mota J. Carbohydr. Res. 197 (1990) 310-317
46. Bock K., and Pedersen C. Adv. Carbohydr. Chem. Biochem. 41 (1983) 27-67