Stereoselective synthesis of substituted exo-glycals from 1-exo-methylene pyranoses

Tetrahedron Letters

Volumn 44, Issue 32, 2003, Pages 6111-6116

  Gómez, Ana M ^a   Pedregosa, Ana ^a   Valverde, Serafín ^a   López, J Cristóbal ^a  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2,6 ANHYDRO 3,4,5,7 TETRA O BENZYL 1 DEOXY 1 (3 PYRIDYL) DEXTRO GALACTOHEPT 1 ENITOL; 2,6 ANHYDRO 3,4,5,7 TETRA O BENZYL 1 DEOXY 1 (3 PYRIDYL) DEXTRO GLUCOHEPT 1 ENITOL; 2,6 ANHYDRO 3,4,5,7 TETRA O BENZYL 1 DEOXY 1 (3 PYRIDYL) DEXTRO MANNOHEPT 1 ENITOL; 2,6 ANHYDRO 3,4,5,7 TETRA O BENZYL 1 DEOXY 1 (3 THIOPHENYL) DEXTRO GALACTOHEPT 1 ENITOL; 2,6 ANHYDRO 3,4,5,7 TETRA O BENZYL 1 DEOXY 1 (3 THIOPHENYL) DEXTRO GLUCOHEPT 1 ENITOL; 2,6 ANHYDRO 3,4,5,7 TETRA O BENZYL 1 DEOXY 1 (3 THIOPHENYL) DEXTRO MANNOHEPT 1 ENITOL; 2,6 ANHYDRO 3,4,5,7 TETRA O BENZYL 1 DEOXY 1 (4 METHOXYPHENOL) DEXTRO GALACTOHEPT 1 ENITOL; 2,6 ANHYDRO 3,4,5,7 TETRA O BENZYL 1 DEOXY 1 (4 METHOXYPHENOL) DEXTRO GLUCOHEPT 1 ENITOL; 2,6 ANHYDRO 3,4,5,7 TETRA O BENZYL 1 DEOXY 1 (4 METHOXYPHENOL) DEXTRO MANNOHEPT 1 ENITOL; 2,6 ANHYDRO 3,4,5,7 TETRA O BENZYL 1 DEOXY 1 (4 TOLYL) DEXTRO GALACTOHEPT 1 ENITOL; 2,6 ANHYDRO 3,4,5,7 TETRA O BENZYL 1 DEOXY 1 (4 TOLYL) DEXTRO GLUCOHEPT 1 ENITOL; 2,6 ANHYDRO 3,4,5,7 TETRA O BENZYL 1 DEOXY 1 (4 TOLYL) DEXTRO MANNOHEPT 1 ENITOL; ALKYL GROUP; BORANE DERIVATIVE; BORONIC ACID DERIVATIVE; CARBENE; CARBOHYDRATE DERIVATIVE; IODONIUM DICOLLIDINIUM TRIFLATE; PYRAN DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; STEREOCHEMISTRY;

LATEOLABRAX JAPONICUS;

EID: 0037964812     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01455-2     Document Type: Article

References (62)

1. Wilcox C.S., Long G.W., Suh H. Tetrahedron Lett. 25:1984;395.
2. Rajanbabu T.V., Reddy G.S. J. Org. Chem. 51:1986;5458.
3. For a review, see: Taylor R.J.K. Chem. Commun. 1999;217.
4. Brockhaus M., Lehmann J. Carbohydr. Res. 53:1977;349.
5. Lehmann J., Schwesinger B. Carbohydr. Res. 107:1982;43.
6. Fritz H., Lehmann J., Schlesselmann P. Carbohydr. Res. 113:1983;71.
7. Hehre E.J., Brewer C.F., Uchiyama T., Schlesselmann P., Lehmann J. Biochemistry. 19:1980;3557.
8. Thiem J., Kleeberg M. Carbohydr. Res. 205:1990;333.
9. Noort D., Veeneman G.H., Boons G.-J.P.H., van der Marel G.A., Mulder G.J., van Boom J.H. Synlett. 1990;205.
10. Nicotra F., Panza L., Russo G. Tetrahedron Lett. 32:1991;4035.
11. Lay L., Nicotra F., Panza L., Russo G., Caneva E. J. Org. Chem. 57:1992;1304.
12. Lay L., Nicotra F., Panza L., Russo G. Synlett. 1995;167.
13. Cipolla L., Liguori L., Nicotra F., Torri G., Vismara E. Chem. Commun. 1996;1253.
14. Lay L., Nicotra F., Panza L., Russo G., Sello G. J. Carbohydr. Chem. 17:1998;1269.
15. Link J.T., Gallant M., Danishefsky S.J. J. Am. Chem. Soc. 115:1993;3782.
16. Gervay J., Flaherty T.M., Holmes D. Tetrahedron. 53:1997;16335.
17. Johnson C.R., Johns B.A. Synlett. 1997;1406.
18. Johns B.A., Pan Y.T., Elbein A.D., Johnson C.R. J. Am. Chem. Soc. 119:1997;4856.
19. Alcaraz M.-L., Griffin F.K., Paterson D.E., Taylor R.J.K. Tetrahedron Lett. 39:1998;8183. and references cited therein.
20. Griffin F.K., Paterson D.E., Taylor R.J.K. Angew. Chem., Int. Ed. 38:1999;2939.
21. Campbell A.D., Paterson D.E., Raynham T.M., Taylor R.J.K. Chem. Commun. 1999;1599.
22. Paterson D.E., Griffin F.K., Alcaraz M.-L., Taylor R.J.K. Eur. J. Org. Chem. 2002;1323.
23. Haase W.C., Nieger M., Dötz K.H. Chem. Eur. J. 5:1999;2014.
24. Sasaki M., Fuwa H., Ishikawa M., Tachibana K. Org. Lett. 1:1999;1075.
25. Yang G., Franck R.W., Byun H.-S., Bittman R., Samadder P., Arthur G. Org. Lett. 1:1999;2149.
26. Pasetto P., Chen X.C., Drain M., Franck R.W. Chem. Commun. 2000;81.
27. Gallos J.K., Sarli V.C., Koftis T.V., Coutouli-Argyropoulou E. Tetrahedron Lett. 41:2000;4819.
28. Ali M.H., Collins P.M., Overend W.G. Carbohydr. Res. 205:1990;428.
29. Csuk R., Glänzer B.I. Tetrahedron. 47:1991;1655.
30. Audrechy A., Sinaÿ P. J. Org. Chem. 57:1992;4142.
31. Faivre-Buet V., Eynard I., Nga H.N., Descotes G., Grouiller A. J. Carbohydr. Chem. 12:1993;349.
32. Tóth M., Somsák L. J. Chem. Soc., Perkin Trans. 1. 2001;942.
33. Ousset J.B., Mioskowski C., Yang Y.-L., Falck J.R. Tetrahedron Lett. 25:1984;5903.
34. Lieberknecht A., Griesser H., Bravo R.D., Colinas P.A., Grigera R.J. Tetrahedron. 54:1998;3159.
35. Lakhrissi M., Chapleur Y. J. Org. Chem. 59:1994;5752.
36. Lakhrissi M., Chapleur Y. Angew. Chem., Int. Ed. Engl. 35:1996;750.
37. Molina A., Czernecki S., Xie J. Tetrahedron Lett. 39:1998;7507.
38. Xie J., Molina A., Czernecki S. J. Carbohydr. Chem. 18:1999;481.
39. Praly J.-P., Chen G.-R., Gola J., Hetzer G., Raphoz C. Tetrahedron Lett. 38:1997;8185.
40. Praly J.-P., Chen G.-R., Gola J., Hetzer G. Eur. J. Org. Chem. 2000;2831.
41. Lay L., Meldal M., Nicotra F., Panza L., Russo G. J. Chem. Soc., Chem. Commun. 1997;1469.
42. Yang W.-B., Chang C.-F., Wang S.-H., Teo C.-F., Lin C.-H. Tetrahedron Lett. 42:2001;4657.
43. Yang W.-B., Bu C.-Y., Chang C.-C., Wang S.-H., Teo C.-F., Lin C.-H. Tetrahedron Lett. 42:2001;6907.
44. Yang W.-B., Yang Y.-Y., Gu Y.F., Wang S.-H., Chang C.-C., Lin C.-H. J. Org. Chem. 67:2002;3773.
45. Griffin F.K., Murphy P.V., Paterson D.E., Taylor R.J.K. Tetrahedron Lett. 39:1998;8179.
46. Griffin F.K., Paterson D.E., Murphy P.V., Taylor R.J.K. Eur. J. Org. Chem. 2002;1305.
47. Belica P.S., Franck R.W. Tetrahedron Lett. 39:1998;8225.
48. Gómez A.M., Pedregosa A., Valverde S., López J.C. Chem. Commun. 2002;2022.
49. Gómez A.M., Danelón G.O., Pedregosa A., Valverde S., López J.C. Chem. Commun. 2002;2024.
50. Veeneman G.H., Van Leeuwen S.H., Zuurmond H., Van Boom J.H. J. Carbohydr. Chem. 9:1990;783.
51. Miyaura N., Suzuki A. Chem. Rev. 95:1995;2457.
52. Suzuki A. Diederich F., Stang P.J. Metal-Catalyzed Cross-Coupling Reactions. 1998;49-97 VCH, Weinheim.
53. Suzuki A. J. Organomet. Chem. 576:1999;147.
54. Chemler S.R., Trauner D., Danishefsky S.J. Angew. Chem., Int. Ed. 40:2001;4544.
55. Overkleeft H.S., van Wiltenburg J., Pandit U. Tetrahedron. 50:1994;4215.
56. Petasis N.A., Bzowej E.I. J. Am. Chem. Soc. 112:1990;6392.
57. Lancelin J.-M., Pougny J.-R., Sinaÿ P. Carbohydr. Res. 136:1985;369.
58. Cipolla L., Liguori L., Nicotra F., Torri G., Vismara E. J. Chem. Soc., Chem. Commun. 1996;1253.
59. Littke A.F., Dai C., Fu G.C. J. Am. Chem. Soc. 122:2000;4020.
60. 4), filtered and concentrated. Flash chromatography of the residue (hexane:EtOAc) furnished the corresponding substituted glycal.
61. 4 (10%, 0.015 equiv.) was added. The reaction mixture was heated at reflux, under argon, for the time indicated in Table 1. Work-up as above then furnished the expected glycals.
62. abstract