Synthesis of 1-Deoxy-D-galactohomonojirimycin via Enantiomerically Pure Allenylstannanes

Journal of Organic Chemistry

Volumn 69, Issue 7, 2004, Pages 2229-2234

  Achmatowicz, Michal ^a   Hegedus, Louis S ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; ALDEHYDES; CATALYSIS; REACTION KINETICS;

DIASTEREOSELECTIVITY; OPTICALLY PURE;

SYNTHESIS (CHEMICAL);

1 DEOXY DEXTRO GALACTOHOMONOJIRIMYCIN; ALDEHYDE; ALLENYLSTANNANE; AMINOALCOHOL; LACTIC ACID; LEWIS ACID; PIPERIDINE DERIVATIVE; TIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DIASTEREOISOMER; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

ALDEHYDES; ALKALOIDS; CATALYSIS; CYCLIZATION; GALACTOSE; INDICATORS AND REAGENTS; LACTIC ACID; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PIPERIDINES; STEREOISOMERISM; TIN;

EID: 1842557448     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0303012     Document Type: Article

References (48)

1. For a review on the mechanism of enzymic glycosyl transfer, see: Sinot, M. L. Chem. Rev. 1990, 90, 1171.
2. For reviews on azasugar inhibitors, see: (a) Bols, M. Acc. Chem. Res. 1998, 31, 1.
3. (b) Ganem, B. Acc. Chem. Res. 1996, 29, 340.
4. (c) Sears, P.; Wong, C. H. Angew. Chem., Int. Ed. 1999, 38, 2300.
5. (d) Iminosugars as Glycosidase Inhibitors: Nojirimycin and Beyond; Stutz, A. E., Ed.; Wiley-VCH: Weinheim, Germany, 1999.
6. For recent reviews, see: (a) Yoda, H. Curr. Org. Chem. 2002, 6, 223.
7. (b) Asano, N.; Hashimoto, H. Glycosciences 2001, 3, 2541.
8. (c) Kazmaier, U. Recent Res. Dev. Org. Chem. 1998, 2 (part 2), 351.
9. For recent synthetic efforts, see the following and the references therein: (a) Han, H. Tetrahedron Lett. 2003, 44, 157.
10. (b) Sawada, D.; Takahashi, H.; Ikegami, S. Tetrahedron Lett. 2003, 44, 3085.
11. For reviews, see: (c) Pandit, U. K.; Overkleeft, H. S.; Borer, B. C.; Bieräugel, H. Eur. J. Org. Chem. 1999, 959.
12. (d) Zhow, W.-S.; Lu, Z.-H.; Xu, Y.-M.; Liao, L.-X.; Wang, Z.-M. Tetrahedron 1999, 55, 11959.
13. (a) Somfai, P.; Marchand, P.; Torsell, S.; Lindström, U. M. Tetrahedron 2093, 59, 1293.
14. (b) Comins, D. L.; Fulp, A. B. Tetrahedron Lett. 2001, 42, 6839.
15. (c) Kiguchi, T.; Ninomiya, I.; Naito, T. Tetrahedron 2000, 56, 5819.
16. (d) Matos, C. R. R.; Lopes, R. S. C.; Lopes, C. C. Synthesis 1999, 571.
17. (e) Kazmaier, U.; Grandel, R. Eur. J. Org. Chem. 1998, 1833.
18. (f) Lindström, U. M.; Somfai, P. Tetrahedron Lett. 1998, 39, 7173.
19. (a) Knight, J. G.; Tchabanenko, K. Tetrahedron 2003, 59, 281.
20. (b) Spreitz, J.; Stutz, A. E.; Wrodnigg, T. M. Carbohydr. Res. 2002, 337, 183.
21. (c) Mehta, G.; Mahal, N. Tetrahedron Lett. 2000, 41, 5741.
22. (d) Meyers, A. I.; Andres, C. J.; Resek, J. E.; Woodall, C. C.; McLaughlin, M. A.; Lee, P. H.; Price, D. A. Tetrahedron 1999, 10, 8931.
23. (e) Xu, Y.-M.; Zhou, W.-S. J. Chem. Soc., Perkin Trans. 1 1997, 741.
24. (a) Patil, N. T.; Tilekar, J. N.; Dhavale, D. D. J. Org. Chem. 2001, 66, 1065.
25. (b) Saha, N. N.; Desai, V. N.; Dhavale, D. D. Tetrahedron 2001, 57, 39.
26. (c) Szolcsányi, P.; Gracza, T.; Koman, M.; Prónayová , N.; Liptaj, T. Tetrahedron: Asymmetry 2000, 11, 2579.
27. (d) Szolcsányi, P.; Gracza, T.; Koman, M.; Prónayová , N.; Liptaj, T. Chem. Commun. 2000, 471.
28. (e) Desai, V. N.; Saha, N. N.; Dhavale, D. D. Chem. Commun. 1999, 1719.
29. (f) Compernolle, F.; Joly, G.; Peetars, K.; Toppet, S.; Hoonaert, G. Tetrahedron 1997, 53, 12739.
30. (g) Herders, C.; Schiffer, T. Tetrahedron 1996, 52, 14745.
31. (h) Lundt, I.; Madsen, R. Synthesis 1995, 787.
32. (i) Kilonda, A.; Compernolle, F.; Toppet, S.; Hoornaert, G. J. Tetrahedron Lett. 1994, 48, 9047.
33. (j) Rassu, G.; Pinna, L.; Spanu, P.; Culeddy, N.; Casiraghi, G.; Fava, G. G.; Ferrari, M. B.; Pelosi, G. Tetrahedron 1992, 48, 727.
34. For a review on the use of chiral allenylstannanes in synthesis, see: Marshall, J. A. Chem. Rev. 1996, 96, 31.
35. Ranslow, P. B. D.; Hegedus, L. S.; de los Rios, C. J. Org. Chem. 2003, in press.
36. To the best of our knowledge, this particular diastereoisomer has not previously been synthesized.
37. (a) Chattopadhyay, A.; Dhotare, B. Tetrahedron: Asymmetry 1998, 9, 2715.
38. (b) Vriesma, B. K.; Buter, J.; Kellogg, R. M. J. Org. Chem. 1984, 49, 110.
39. Alemany, C.; Bach, J.; Farras, J.; Garcia, J. Org. Lett. 1999, 1, 1831.
40. Mukaiyama, T. Angew. Chem., Int. Ed. Engl. 1979, 18, 707.
41. (a) Mistunobu, O.; Yamada, M.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1967, 40, 935.
42. (b) Hughes, D. L. Org. React. 1992, 42, 335.
43. (a) Liao, X.; Wu, Y.; DeBrabander, J. K. Angew. Chem., Int. Ed. 2003, 42, 1648.
44. (b) Smith, A. B., III; Safonov, I. G.; Corbett, R. M. J. Am. Chem. Soc. 2002, 124, 11102.
45. (c) Ahn, C.; DeShong, P. J. Org. Chem. 2002, 67, 1754.
46. Silyl migration from the terminal to the internal OH group in 6, followed by cyclization to give an eight-membered lactone, which rearranged to the butyrolactone on subsequent desilylation, was deemed less likely.
47. Compain, P.; Gore, J.; Vatele, J.-M. Tetrahedron 1996, 52, 10405.
48. McDonald, F. E. Chem. Eur. J. 1999, 5, 3103 and references therein.