The asymmetric synthesis of D-galactose via an iterative syn-glycolate aldol strategy

Synlett

Volumn , Issue 10, 2002, Pages 1637-1640

  Davies, Stephen G ^a   Nicholson, Rebecca L ^a   Smith, Andrew D ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

Asymmetric synthesis; D galactose; Iterative glycolate aldol reaction; Monosaccharides

Indexed keywords

GALACTOSE; GLYCOLIC ACID DERIVATIVE;

ARTICLE; CARBOHYDRATE SYNTHESIS; CRYSTALLIZATION; CYCLIZATION; HYDROGENATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REDUCTION;

EID: 0036400051     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-34215     Document Type: Article

References (53)

1. Danishefsky, S. J.; DeNinno, M. P. Angew. Chem., Int. Ed. Engl. 1987, 26, 15.
2. (a) Bednarski, M.; Danishefsky, S. J. Am. Chem. Soc. 1983, 105, 6968.
3. (b) Danishefsky, S. J.; Larson, E.; Springer, J. P. J. Am. Chem. Soc. 1985, 107, 1274.
4. (c) Danishefsky, S. J.; Pearson, W. H.; Segmuller, B. E. J. Am. Chem. Soc. 1985, 107, 1280.
5. (d) Bednarski, M.; Danishefsky, S. J. Am. Chem. Soc. 1986, 108, 7060.
6. (e) Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 403.
7. (a) Harris, J. M.; Keränen, M. D.; Nguyen, H.; Young, V. G.; O'Doherty, G. A. Carbohydr. Res. 2000, 328, 17.
8. (b) Henderson, I.; Sharpless, K. B.; Wong, C.-H. J. Am. Chem. Soc. 1994, 116, 558.
9. (c) Kobayashi, S.; Kawasuji, T. Synlett 1993, 911.
10. (a) Gijsen, H. J. M.; Qiao, L.; Fitz, W.; Wong, C.-H. Chem. Rev. 1996, 96, 443.
11. (b) Hudlicky, T.; Pitzer, K. K.; Stabile, M. R.; Thorpe, A. J.; Whited, G. M. J. Org. Chem. 1996, 61, 4151.
12. (c) Johnson, C. R.; Golebiowski, A.; Steensma, D. H. J. Am. Chem. Soc. 1992, 114, 9414.
13. (a) Takeuchi, M.; Tanguchi, T.; Ogasawara, K. Chirality 2000, 338.
14. (b) Marshall, J. A.; Hinkle, K. W. J. Org. Chem. 1996, 61, 105.
15. (c) Kobayashi, S.; Wakabayashi, T.; Yasuda, M. J. Org. Chem. 1998, 63, 4868.
16. (d) Evans, D. A.; Ng, H. P. Tetrahedron Lett. 1993, 34, 2229.
17. (a) Koo, S. Y.; Lee, A. W. M.; Masamune, S.; Reed, L. A. I. I. I.; Sharpless, K. B.; Walker, F. J. Science 1983, 220, 949.
18. (b) Koo, S. Y.; Lee, A. W. M.; Masamune, S.; Reed, L. A. III.; Sharpless, K. B.; Walker, F. J. Tetrahedron 1990, 46, 245.
19. (a) Golec, J. M. C.; Jones, S. D. Tetrahedron Lett. 1993, 50, 8159.
20. (b) Evans, D. A.; Miller, S. J.; Ennis, M. D.; Ornstein, P. L. J. Org. Chem. 1992, 57, 1067.
21. For leading examples of iterative aldo1 approaches to polypropionate fragments on solid phase see: (a) Paterson, I.; Donghi, M.; Gerlach, K. Angew. Chem. Int. Ed. 2000, 39, 3315. (b) Reggelin, M.; Brenig, V. Tetrahedron Lett. 1996, 38, 6851. (c) For solution phase synthesis see: Paterson, I.; Scott, J. P. Tetrahedron Lett. 1997, 42, 7441. (d) Also see: Paterson, I.; Scott, J. P. J. Chem. Soc., Perkin Trans. 1. 1999, 1003.
22. For leading examples of iterative aldo1 approaches to polypropionate fragments on solid phase see: (a) Paterson, I.; Donghi, M.; Gerlach, K. Angew. Chem. Int. Ed. 2000, 39, 3315. (b) Reggelin, M.; Brenig, V. Tetrahedron Lett. 1996, 38, 6851. (c) For solution phase synthesis see: Paterson, I.; Scott, J. P. Tetrahedron Lett. 1997, 42, 7441. (d) Also see: Paterson, I.; Scott, J. P. J. Chem. Soc., Perkin Trans. 1. 1999, 1003.
23. For leading examples of iterative aldo1 approaches to polypropionate fragments on solid phase see: (a) Paterson, I.; Donghi, M.; Gerlach, K. Angew. Chem. Int. Ed. 2000, 39, 3315. (b) Reggelin, M.; Brenig, V. Tetrahedron Lett. 1996, 38, 6851. (c) For solution phase synthesis see: Paterson, I.; Scott, J. P. Tetrahedron Lett. 1997, 42, 7441. (d) Also see: Paterson, I.; Scott, J. P. J. Chem. Soc., Perkin Trans. 1. 1999, 1003.
24. For leading examples of iterative aldo1 approaches to polypropionate fragments on solid phase see: (a) Paterson, I.; Donghi, M.; Gerlach, K. Angew. Chem. Int. Ed. 2000, 39, 3315. (b) Reggelin, M.; Brenig, V. Tetrahedron Lett. 1996, 38, 6851. (c) For solution phase synthesis see: Paterson, I.; Scott, J. P. Tetrahedron Lett. 1997, 42, 7441. (d) Also see: Paterson, I.; Scott, J. P. J. Chem. Soc., Perkin Trans. 1. 1999, 1003.
25. (a) Crimmins, M. T.; Tabet, E. A. J. Am. Chem. Soc. 2000, 122, 5473.
26. (b) Li, Z.; Wu, R.; Michalczyk, R.; Dunlap, R. B.; Odom, J. D.; Silks, L. A. P. III J. Am. Chem. Soc. 2000, 122, 386.
27. (c) Hunziker, D.; Wu, N.; Kenoshita, K.; Cane, D. E.; Khosla, C. Tetrahedron Lett. 1999, 40, 635.
28. The reactivity of glycolate enolates have been extensively reported. For glycolate enolate alkylations see: (a) Crimmins, M. T.; Emmitte, K. A.; Katz, J. D. Org. Lett. 2000, 2, 2165. (b) Burke, S. D.; Quinn, K. J.; Chen, V. J. J. Org. Chem. 1998, 63, 8626. (c) For glycolate enolate additions to acyclic ketimines see: Bravo, P.; Fustero, S.; Guidetti, M.; Volonterio, A.; Zanda, M. J. Org. Chem. 1999, 64, 8731.
29. The reactivity of glycolate enolates have been extensively reported. For glycolate enolate alkylations see: (a) Crimmins, M. T.; Emmitte, K. A.; Katz, J. D. Org. Lett. 2000, 2, 2165. (b) Burke, S. D.; Quinn, K. J.; Chen, V. J. J. Org. Chem. 1998, 63, 8626. (c) For glycolate enolate additions to acyclic ketimines see: Bravo, P.; Fustero, S.; Guidetti, M.; Volonterio, A.; Zanda, M. J. Org. Chem. 1999, 64, 8731.
30. The reactivity of glycolate enolates have been extensively reported. For glycolate enolate alkylations see: (a) Crimmins, M. T.; Emmitte, K. A.; Katz, J. D. Org. Lett. 2000, 2, 2165. (b) Burke, S. D.; Quinn, K. J.; Chen, V. J. J. Org. Chem. 1998, 63, 8626. (c) For glycolate enolate additions to acyclic ketimines see: Bravo, P.; Fustero, S.; Guidetti, M.; Volonterio, A.; Zanda, M. J. Org. Chem. 1999, 64, 8731.
31. For representative examples of other glycolate aldol reactions see: (a) Roush, W. R.; Pfeifer, L. A.; Marron, T. G. J. Org. Chem. 1998, 63, 2064. (b) Kim, K. S.; Hong, S. D. Tetrahedron Lett. 2000, 41, 5909. (c) Sasaki, S.; Hamada, Y.; Shioiri, T. Tetrahedron Lett. 1999, 40, 3187. (d) Andrus, M. B.; Soma Sekhar, B. B. V.; Turner, T. M.; Meredith, E. L. Tetrahedron Lett. 2001, 42, 7197.
32. For representative examples of other glycolate aldol reactions see: (a) Roush, W. R.; Pfeifer, L. A.; Marron, T. G. J. Org. Chem. 1998, 63, 2064. (b) Kim, K. S.; Hong, S. D. Tetrahedron Lett. 2000, 41, 5909. (c) Sasaki, S.; Hamada, Y.; Shioiri, T. Tetrahedron Lett. 1999, 40, 3187. (d) Andrus, M. B.; Soma Sekhar, B. B. V.; Turner, T. M.; Meredith, E. L. Tetrahedron Lett. 2001, 42, 7197.
33. For representative examples of other glycolate aldol reactions see: (a) Roush, W. R.; Pfeifer, L. A.; Marron, T. G. J. Org. Chem. 1998, 63, 2064. (b) Kim, K. S.; Hong, S. D. Tetrahedron Lett. 2000, 41, 5909. (c) Sasaki, S.; Hamada, Y.; Shioiri, T. Tetrahedron Lett. 1999, 40, 3187. (d) Andrus, M. B.; Soma Sekhar, B. B. V.; Turner, T. M.; Meredith, E. L. Tetrahedron Lett. 2001, 42, 7197.
34. For representative examples of other glycolate aldol reactions see: (a) Roush, W. R.; Pfeifer, L. A.; Marron, T. G. J. Org. Chem. 1998, 63, 2064. (b) Kim, K. S.; Hong, S. D. Tetrahedron Lett. 2000, 41, 5909. (c) Sasaki, S.; Hamada, Y.; Shioiri, T. Tetrahedron Lett. 1999, 40, 3187. (d) Andrus, M. B.; Soma Sekhar, B. B. V.; Turner, T. M.; Meredith, E. L. Tetrahedron Lett. 2001, 42, 7197.
35. Bull, S. D.; Davies, S. G.; Jones, S.; Sanganee, H. J. J. Chem. Soc., Perkin Trans. 1 1999, 387.
36. (a) Bach, J.; Bull, S. D.; Davies, S. G.; Nicholson, R. L.; Sanganee, H. J.; Smith, A. D. Tetrahedron Lett. 1999, 40, 6677.
37. (b) Bull, S. D.; Davies, S. G.; Nicholson, R. L.; Sanganee, H. J.; Smith, A. D. Tetrahedron: Assymmetry 2000, 11, 3475.
38. (a) Evans, D. A.; Bartroli, J. Tetrahedron Lett. 1982, 23, 807.
39. (b) Evans, D. A.; Polniaszek, R. P.; DeVries, K. M.; Guinn, D. E.; Mathre, D. J. J. Am. Chem. Soc. 1991, 113, 7613.
40. (c) Chakraborty, T. K.; Suresh, V. R. Tetrahedron Lett. 1998, 39, 7775.
41. (d) Brimble, M. A.; Naim, M. R.; Park, J. Org. Lett. 1999, 1, 1459.
42. (e) An alternative strategy involving conversion to the Weinreb amide and subsequent reduction has also been employed, see: Evans, D. A.; Miller, S. J.; Ennis, M. D. J. Org. Chem. 1993, 58, 471.
43. The reduction of N-acyl thiaoxazolidinones to aldehydes has previously been reported, see: (a) Chakraborty, T. K.; Jayaprakash, S.; Lazman, P. Tetrahedron 2001, 57, 9461. (b) Izawa, T.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1979, 52, 555. (c) Izawa, T.; Mukaiyama, T. Chem. Lett. 1977, 1443. (d) For an isolated example of the direct Red-Al reduction of an N-acyl oxazolidinone to an aldehyde see: Meyers, A. I.; Spohn, R. F.; Linderman, R. J. J. Org. Chem. 1985, 50, 3633.
44. The reduction of N-acyl thiaoxazolidinones to aldehydes has previously been reported, see: (a) Chakraborty, T. K.; Jayaprakash, S.; Lazman, P. Tetrahedron 2001, 57, 9461. (b) Izawa, T.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1979, 52, 555. (c) Izawa, T.; Mukaiyama, T. Chem. Lett. 1977, 1443. (d) For an isolated example of the direct Red-Al reduction of an N-acyl oxazolidinone to an aldehyde see: Meyers, A. I.; Spohn, R. F.; Linderman, R. J. J. Org. Chem. 1985, 50, 3633.
45. The reduction of N-acyl thiaoxazolidinones to aldehydes has previously been reported, see: (a) Chakraborty, T. K.; Jayaprakash, S.; Lazman, P. Tetrahedron 2001, 57, 9461. (b) Izawa, T.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1979, 52, 555. (c) Izawa, T.; Mukaiyama, T. Chem. Lett. 1977, 1443. (d) For an isolated example of the direct Red-Al reduction of an N-acyl oxazolidinone to an aldehyde see: Meyers, A. I.; Spohn, R. F.; Linderman, R. J. J. Org. Chem. 1985, 50, 3633.
46. The reduction of N-acyl thiaoxazolidinones to aldehydes has previously been reported, see: (a) Chakraborty, T. K.; Jayaprakash, S.; Lazman, P. Tetrahedron 2001, 57, 9461. (b) Izawa, T.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1979, 52, 555. (c) Izawa, T.; Mukaiyama, T. Chem. Lett. 1977, 1443. (d) For an isolated example of the direct Red-Al reduction of an N-acyl oxazolidinone to an aldehyde see: Meyers, A. I.; Spohn, R. F.; Linderman, R. J. J. Org. Chem. 1985, 50, 3633.
47. 2, washed with brine, dried and concentrated in vacuo before purification by flash column chromatography.
48. 4Cl solution and stirred for a further 20 minutes. The resultant emulsion was filtered through Celite®, dried and concentrated in vacuo before purification by flash column chromatography.
49. BPh], 7.27-7.37 (10 H, m, PhH), 9.76 (1 H, d, J = 1.3 Hz, CHO).
50. (a) Smith, A. B. III; Ott, G. R. J. Am. Chem. Soc. 1996, 118, 13095.
51. (b) Smith, A. B. III; Chen, S. S.-Y.; Nelson, F. C.; Reichert, R. C.; Salvatore, B. A. J. Am. Chem. Soc. 1995, 117, 12017.
52. BPh], 7.21-7.43 (15 H, m, PhH).
53. Commercially available from the Aldrich Chemical company.