Synthesis of l-altro-1-deoxynojirimycin, d-allo-1-deoxynojirimycin, and d-galacto-1-deoxynojirimycin from a single chiral cyanohydrin

Organic Letters

Volumn 12, Issue 17, 2010, Pages 3957-3959

  Van Den Nieuwendijk, Adrianus M C H ^a   Ruben, Mark ^a   Engelsma, Sander E ^a   Risseeuw, Martijn D P ^a   Van Den Berg, Richard J B H N ^a   Boot, Rolf G ^c   Aerts, Johannes M ^c   Brussee, Johannes ^b   Van Der Marel, Gijs A ^a   Overkleeft, Herman S ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

^b LEIDEN UNIVERSITY   (Netherlands)

^c ACADEMIC MEDICAL CENTER   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

1 DEOXYNOJIRIMYCIN; ACETONE CYANOHYDRIN LYASE; ACETONE-CYANOHYDRIN LYASE; CYANOHYDRIN; D ALLO 1 DEOXYNOJIRIMYCIN; D GALACTO 1 DEOXYNOJIRIMYCIN; D-ALLO-1-DEOXYNOJIRIMYCIN; D-GALACTO-1-DEOXYNOJIRIMYCIN; DRUG DERIVATIVE; L ALTRO 1 DEOXYNOJIRIMYCIN; L-ALTRO-1-DEOXYNOJIRIMYCIN; LYASE; NITRILE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; ENZYMOLOGY; METABOLISM; PRUNUS; STEREOISOMERISM; SYNTHESIS;

1-DEOXYNOJIRIMYCIN; ALDEHYDE-LYASES; CYCLIZATION; MOLECULAR STRUCTURE; NITRILES; PRUNUS; STEREOISOMERISM;

EID: 77956224500     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol101556k     Document Type: Article

References (45)

1. For selected reviews, see
2. Holt, J.; Hanefeld, U. Curr. Org. Synth. 2009, 6, 15-37
3. Brunel, J.-M.; Holmes, I. P. Angew. Chem., Int. Ed. 2004, 43, 2752-2778
4. North, M. Tetrahedron: Asymmetry 2003, 14, 147-176
5. Gregory, R. J. H. Chem. Rev. 1999, 99, 3649-3682
6. Ziegler, T.; Hörsch, B.; Effenberger, F. Synthesis 1990, 575-578
7. Brussee, J.; Loos, W. T.; van der Gen, A. Tetrahedron 1990, 46, 979-986
8. Brussee, J.; Dofferhof, F.; Kruse, C. G.; van der Gen, A. Tetrahedron 1990, 46, 1653-1658
9. Zandbergen, P.; van den Nieuwendijk, A. M. C. H.; Brussee, J.; van der Gen, A.; Kruse, C. G. Tetrahedron 1992, 48, 3977-3982
10. Avi, M; Gaiberger, R.; Feichtenhofer, S.; Griengl, H. Tetrahedron 2009, 65, 5418-5426
11. Effenberger, F.; Stelzer, U. Tetrahedron: Asymmetry 1995, 6, 283-286
12. Ritzen, M.; van Oers, M. C. M.; van Delft, F.; Rutjes, F. P. J. T. J. Org. Chem. 2009, 74, 7548-7551
13. Monterde, M. I.; Nazabadioko, S.; Rebolledo, F.; Brieva, R.; Gotor, V. Tetrahedron: Asymmetry 1999, 10, 3449-3455
14. van den Nieuwendijk, A. M. C. H.; Ghisaidoobe, A. B. T.; Overkleeft, H. S.; Brussee, J.; van der Gen, A. Tetrahedron 2004, 60, 10385-10396
15. Johnson, D. V.; Felfer, U.; Griengl, H. Tetrahedron 2000, 56, 781-790
16. Tromp, R. A.; van der Hoeven, M.; Amore, A.; Brussee, J.; Overhand, M.; van der Marel, G. A.; van der Gen, A. Tetrahedron: Asymmetry 2001, 12, 1109-1112
17. Zandbergen, P.; Brussee, J.; van der Gen, A.; Kruse, C. G. Tetrahedron: Asymmetry 1992, 3, 769-774
18. Zandbergen, P.; van der Linden, J.; Brussee, J.; van der Gen, A. Synth. Commun. 1991, 21, 1387-1391
19. Campbell, A. D.; Raynham, T. M.; Taylor, R. J. K. Synthesis 1998, 1707-1709
20. Barrow, J. C.; Ngo, P. L.; Pellicore, J. M.; Selnick, H. G.; Nantermet, P. G. Tetrahedron Lett. 2001, 42, 2051-2054
21. Tang, P. T.; Volkman, S. K.; Ellman, J. A. J. Org. Chem. 2001, 66, 8772-8778
22. For an excellent review on the chemistry of chiral sulfinimides, see
23. Robak, M. T.; Herbage, M. A.; Ellman, J. A. Chem. Rev. 2010, 110, 3600-3740
24. Ritzen, B.; Hoekman, S.; Durán Verdasco, E.; van Delft, F. J.; Rutjes, F. P. J. T. J. Org. Chem. 2010, 75, 3461-3464
25. Examples of analytical data: compound 17 (i) Ikota, N.; Hirano, J.-I.; Gamage, R.; Nakagawa, H.; Hama-Inaba, H. Heterocycles 1997, 46, 637-644.
26. Gupta, P.; Vankar, Y. D. Eur. J. Org. Chem. 2009, 1925-1933
27. Compound 18: (i) Ruiz, M.; Ruanova, T. M.; Blanco, O.; Núñez, F.; Pato, C.; Ojea, V. J. Org. Chem. 2008, 73, 2240-2255.
28. Paulsen, H.; Hayauchi, Y.; Sinnwell, V. Chem. Ber. 1980, 113, 2601-2608.
29. McDonnell, C.; Cronin, L.; O'Brien, J. L.; Murphy, P. V. J. Org. Chem. 2004, 69, 3565-3568 Compound 20
30. Dhavale, D. D.; Markad, S. D.; Karanjule, N. S.; PrakashaReddy, J. J. Org. Chem. 2004, 69, 4760-4766.
31. Barili, P. R.; Berti, G.; D'Andrea, F.; Rensis, D. E.; Puccioni, L. Tetrahedron 1997, 53, 3407-3416
32. For reviews see
33. Compain, P.; Chagnault, V.; Martin, O. R. Tetrahedron: Asymmetry 2009, 20, 672-711
34. Compain, P.; Martin, O. R., Eds. Iminosugars: From Synthesis to Therapeutic Applications; Wiley-VCH: Weinheim, 2007.
35. Cipolla, L.; La Ferla, B.; Nicotra, F. Curr. Top. Med. Chem. 2003, 3, 485-511
36. For recent examples, see
37. Bagal, S. K.; Davies, S. G.; Lee, J. A.; Roberts, P. M.; Russell, A. J.; Scott, P. M.; Thomson, J. E. Org. Lett. 2010, 12, 136-139
38. Takahata, H.; Banba, Y.; Ouchi, H.; Nemoto, H. Org. Lett. 2003, 5, 2527-2529
39. Takahata, H.; Banba, Y.; Sasatani, M.; Nemoto, H.; Kato, A.; Adachi, I. Tetrahedron 2004, 60, 8199-8205
40. Ruiz, M.; Ruanova, T. M.; Blanco, O.; Núñez, F.; Pato, C.; Ojea, V. J. Org. Chem. 2008, 73, 2240-2255
41. Best, D.; Wang, C.; Weymouth-Wilson, A. C.; Clarkson, R. A.; Wilson, F. X.; Nash, R. J.; Miyauchi, S.; Kato, A.; Fleet, G. W. J. Tetrahedron: Asymmetry 2010, 21, 311-319
42. Wennekes, T.; van den Berg, R. J. B. H. N.; Boltje, T. J.; Donker-Koopman, W. E.; Kuijper, B.; van der Marel, G. A.; Strijland, A.; Verhagen, C. P.; Aerts, J. M. F. G.; Overkleeft, H. S. Eur. J. Org. Chem. 2010, 1258-1283
43. Wennekes, T.; van den Berg, R. J. B. H. N.; Boot, R. G.; van der Marel, G. A.; Overkleeft, H. S.; Aerts, J. M. F. G. Angew. Chem., Int. Ed. 2009, 48, 8848-8869
44. Wennekes, T.; van den Berg, R. J. B. H. N.; Donker, W.; van der Marel, G. A.; Strijland, A.; Aerts, J. M. F. G.; Overkleeft, H. S. J. Org. Chem. 2007, 72, 1088-1097
45. Wennekes, T.; Meijer, A. J.; Groen, A. K.; Boot, R. G.; Groener, J. E.; van Eijk, M.; Ottenhoff, R.; Bijl, N.; Ghauharali, K.; Song, H.; O'Shea, T. J.; Liu, H. L.; Yew, N.; Copeland, D.; van den Berg, R. J. B. H. N.; van der Marel, G. A.; Overkleeft, H. S.; Aerts, J. M. J. Med. Chem. 2010, 53, 689-698