Convergent stereocontrolled synthesis of substituted exo-glycals by Stille cross-coupling of halo-exo-glycals and stannanes

Tetrahedron Letters

Volumn 47, Issue 35, 2006, Pages 6243-6246

  Gómez, Ana M ^a   Barrio, Aitor ^a   Amurrio, Iñigo ^a   Valverde, Serafín ^a   Jarosz, Slawomir ^b   López, J Cristóbal ^a  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

^b INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; GLYCOSIDASE INHIBITOR; TIN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; STILLE REACTION; SUBSTITUTION REACTION;

EID: 33746298940     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.06.133     Document Type: Article

References (56)

1. Wilcox C.S., Long G.W., and Suh H. Tetrahedron Lett. 25 (1984) 395-398
2. Rajanbabu T.V., and Reddy G.S. J. Org. Chem. 51 (1986) 5458-5461
3. Reviews:. Taillefumier C., and Chapleur Y. Chem. Rev. 104 (2004) 263-292
4. Taylor R.J.K. Chem. Commun. (1999) 217-227
5. Brockhaus M., and Lehmann J. Carbohydr. Res. 53 (1977) 21-31
6. Lehmann J., and Schwesinger B. Carbohydr. Res. 107 (1982) 43-53
7. Fritz H., Lehmann J., and Schlesselmann P. Carbohydr. Res. 113 (1983) 71-92
8. Hehre E.J., Brewer C.F., Uchiyama T., Schlesselmann P., and Lehmann J. Biochemistry 19 (1980) 3557-3664
9. Ali M.H., Collins P.M., and Overend W.G. Carbohydr. Res. 205 (1990) 428-434
10. Csuk R., and Glänzer B.I. Tetrahedron 47 (1991) 1655-1664
11. Audrechy A., and Sinaÿ P. J. Org. Chem. 57 (1992) 4142-4151
12. Faivre-Buet V., Eynard I., Nga H.N., Descotes G., and Grouiller A. J. Carbohydr. Chem. 12 (1993) 349-356
13. Molas P., Matheu M.I., and Castillón S. Tetrahedron Lett. 45 (2004) 3721-3724
14. Gueyrard D., Haddoub R., Salem A., Bacar N.S., and Goekjian P.G. Synlett (2005) 520-522
15. Caravano A., Vincent S.P., and Sinaÿ P. Chem. Commun. (2004) 1216-1217
16. Stoltz F., Reiner M., Blume A., Reutter W., and Schmidt R.R. J. Org. Chem. 69 (2004) 665-679
17. Ousset J.B., Mioskowski C., Yang Y.-L., and Falck J.R. Tetrahedron Lett. 25 (1984) 5903-5906
18. Lieberknecht A., Griesser H., Bravo R.D., Colinas P.A., and Grigera R.J. Tetrahedron 54 (1998) 3159-3168
19. Lieberknecht A., Griesser H., Krämer B., Bravo R.D., Colinas P.A., and Grigera R.J. Tetrahedron 55 (1999) 6475-6482
20. Lakhrissi M., and Chapleur Y. J. Org. Chem. 59 (1994) 5752-5757
21. Lakhrissi M., and Chapleur Y. Angew. Chem., Int. Ed. 35 (1996) 750-752
22. Molina A., Czernecki S., and Xie J. Tetrahedron Lett. 39 (1998) 7507-7510
23. Xie J., Molina A., and Czernecki S. J. Carbohydr. Chem. 18 (1999) 481-498
24. Gascón-López M., Motevalli M., Paloumbis G., Bladon P., and Wyatt P.B. Tetrahedron 59 (2003) 9349-9360
25. Praly J.-P., Chen G.-R., Gola J., Hetzer G., and Raphoz C. Tetrahedron Lett. 38 (1997) 8185-8188
26. Praly J.-P., Chen G.-R., Gola J., and Hetzer G. Eur. J. Org. Chem. (2000) 2831-2838
27. Lay L., Meldal M., Nicotra F., Panza L., and Russo G. J. Chem. Soc., Chem. Commun. (1997) 1469-1470
28. Griffin F.K., Murphy P.V., Paterson D.E., and Taylor R.J.K. Tetrahedron Lett. 39 (1998) 8179-8182
29. Griffin F.K., Paterson D.E., Murphy P.V., and Taylor R.J.K. Eur. J. Org. Chem. (2002) 1305-1322
30. Belica P.S., and Franck R.W. Tetrahedron Lett. 39 (1998) 8225-8228
31. Yang W.-B., Chang C.-F., Wang S.-H., Teo C.-F., and Lin C.-H. Tetrahedron Lett. 42 (2001) 4657-4660
32. Yang W.-B., Bu C.-Y., Chang C.-C., Wang S.-H., Teo C.-F., and Lin C.-H. Tetrahedron Lett. 42 (2001) 6907-6910
33. Yang W.-B., Yang Y.-Y., Gu Y.F., Wang S.-H., Chang C.-C., and Lin C.-H. J. Org. Chem. 67 (2002) 3773-3782
34. Gómez A.M., Pedregosa A., Valverde S., and López J.C. Chem. Commun. (2002) 2022-2023
35. Gómez A.M., Danelón G.O., Pedregosa A., Valverde S., and López J.C. Chem. Commun. (2002) 2024-2025
36. Gómez A.M., Pedregosa A., Valverde S., and López J.C. Tetrahedron Lett. (2003) 6111-6116
37. Gómez A.M., Pedregosa A., Barrio A., Valverde S., and López J.C. Tetrahedron Lett. (2004) 6307-6310
38. Stille J.K., and Milstein D. J. Am. Chem. Soc. 100 (1978) 3636-3638
39. Stille J.K. Angew. Chem., Int. Ed. Engl. 25 (1986) 508-524
40. Farina V. Pure Appl. Chem. 68 (1996) 73-78
41. Farina V., Krishnamurthy V., and Scott W.J. Org. React. 50 (1997) 1-652
42. Petasis N.A., and Bzowej E.I. J. Am. Chem. Soc. 112 (1990) 6392-6394
43. Veeneman G.H., Van Leeuwen S.H., Zuurmond H., and Van Boom J.H. J. Carbohydr. Chem. 9 (1990) 783-796
44. Nozaki K., Oshima K., and Utimoto K. J. Am. Chem. Soc. 109 (1987) 2547-2549
45. Nozaki K., Oshima K., and Utimoto K. Tetrahedron 45 (1989) 923-933
46. The reactions were run at 0 °C and the (E)-adducts were obtained as the major, or the sole, reaction compounds. Flash chromatography on silicagel allowed us to isolate the pure (E)-isomers. For an analogous process see:. Gómez A.M., López J.C., and Fraser-Reid B. J. Chem. Soc., Perkin Trans. 1 (1994) 1689-1695
47. General procedure for the preparation of alkenyl-stannanes: To a stirred solution of the terminal alkyne (1.0 mol equiv) and tributyltin hydride (1.1 mol equiv) in toluene (10 mL/mmol) was added triethylborane (0.1 mol equiv of an hexane solution) under argon at 0 °C. The reaction mixture was stirred for 24 h and was then concentrated under reduced pressure. The residue was purified by flash chromatography.
48. 4), filtered, and concentrated. Flash chromatography of the residue (hexane-EtOAc) furnished the corresponding substituted glycal.
49. Mee S.P.H., Lee V., and Baldwin J.E. Angew. Chem., Int. Ed. 43 (2004) 1132-1136
50. Natural products hybrids, see:. Hopen S., Emde U., Friedrich T., Grubert L., and Koert U. Angew. Chem., Int. Ed. 39 (2000) 2099-2102
51. Tietze L.F., Schneider G., Wölfling J., Nöbel T., Wulff C., Schubert I., and Rübeling A. Angew. Chem., Int. Ed. 37 (1998) 2469-2470
52. For the synthesis of terpene-based hybrids:. Alvaro E., de la Torre M.C., and Sierra M.A. Org. Lett. 5 (2003) 2381-2384
53. For the synthesis of sugar-based hybrids: Gómez, A. M.; Uriel, C.; Valverde, S.; López, J. C. Org. Lett., in press, doi:10.1021/oI060929+.
54. Diversity oriented synthesis, see:. Burke M.D., and Schreiber S.L. Angew. Chem., Int. Ed. 43 (2004) 46-58
55. Shang S., and Tan D.S. Curr. Opin. Chem. Biol. 9 (2005) 248-258
56. +.