Stereocontrolled transformation of nitrohexofuranoses into cyclopentylamines via 2-oxabicyclo[2.2.1]heptanes: Incorporation of polyhydroxylated carbocyclic β-amino acids into peptides

Organic Letters

Volumn 5, Issue 9, 2003, Pages 1423-1425

  Soengas, Raquel G ^a   Estévez, Juan C ^a   Estévez, Ramón J ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

BETA AMINO ACID; BICYCLO COMPOUND; FURAN DERIVATIVE; GLUCOSIDASE; HEPTANE; PENTYLAMINE; PEPTIDE; SUGAR; AMINE; AMINO ACID; CARBOXYLIC ACID; CYCLOPENTANE DERIVATIVE; HEXOSE;

ARTICLE; CYCLIZATION; DRUG ACTIVITY; DRUG SYNTHESIS; STEREOCHEMISTRY; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ACIDS, CARBOCYCLIC; AMINES; AMINO ACIDS; CYCLIZATION; CYCLOPENTANES; HEPTANES; HEXOSES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PEPTIDES; STEREOISOMERISM;

EID: 0043268074     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034127f     Document Type: Article

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31. For two recent reviews on inhibitors of glicosidases, see: (a) Asano, N. ; Nash, R. J.; Molyneux, R. J.; Fleet, G. W. J. Tetrahedron: Asymmetry 2000, 11, 1645. (b) Lillelund, V. H.; Jensen, H. H.; Liang, X.; Bols, M. Chem. Rev. 2002, 102, 515. Recent selected articles in this field: (c) Uchida, C.; Ogawa, S. Recent Res. Dev. Pure Appl. Chem. 1999, 3, 161. (d) Leroy, E.; Reymond, J.-L. Org. Lett. 1999, 1, 775. (e) Boss, O.; Leroy, E.; Blaser, A.; Reymond, J.-L. Org. Lett. 2000, 2, 151. (f) Kleban, M.; Hilgers, P.; Greul, J. N.; Kugler, R. D.; Li, Jing; P., Sylviane; V., Pierre; Jager, V. ChemBioChem 2001, 2, 365. (g) Greul, J. N.; Kleban, M.; Schneider, B.; Picasso, S.; Jager, V. ChemBioChem 2001, 2, 368.
32. For two recent reviews on inhibitors of glicosidases, see: (a) Asano, N. ; Nash, R. J.; Molyneux, R. J.; Fleet, G. W. J. Tetrahedron: Asymmetry 2000, 11, 1645. (b) Lillelund, V. H.; Jensen, H. H.; Liang, X.; Bols, M. Chem. Rev. 2002, 102, 515. Recent selected articles in this field: (c) Uchida, C.; Ogawa, S. Recent Res. Dev. Pure Appl. Chem. 1999, 3, 161. (d) Leroy, E.; Reymond, J.-L. Org. Lett. 1999, 1, 775. (e) Boss, O.; Leroy, E.; Blaser, A.; Reymond, J.-L. Org. Lett. 2000, 2, 151. (f) Kleban, M.; Hilgers, P.; Greul, J. N.; Kugler, R. D.; Li, Jing; P., Sylviane; V., Pierre; Jager, V. ChemBioChem 2001, 2, 365. (g) Greul, J. N.; Kleban, M.; Schneider, B.; Picasso, S.; Jager, V. ChemBioChem 2001, 2, 368.
33. For two recent reviews on inhibitors of glicosidases, see: (a) Asano, N. ; Nash, R. J.; Molyneux, R. J.; Fleet, G. W. J. Tetrahedron: Asymmetry 2000, 11, 1645. (b) Lillelund, V. H.; Jensen, H. H.; Liang, X.; Bols, M. Chem. Rev. 2002, 102, 515. Recent selected articles in this field: (c) Uchida, C.; Ogawa, S. Recent Res. Dev. Pure Appl. Chem. 1999, 3, 161. (d) Leroy, E.; Reymond, J.-L. Org. Lett. 1999, 1, 775. (e) Boss, O.; Leroy, E.; Blaser, A.; Reymond, J.-L. Org. Lett. 2000, 2, 151. (f) Kleban, M.; Hilgers, P.; Greul, J. N.; Kugler, R. D.; Li, Jing; P., Sylviane; V., Pierre; Jager, V. ChemBioChem 2001, 2, 365. (g) Greul, J. N.; Kleban, M.; Schneider, B.; Picasso, S.; Jager, V. ChemBioChem 2001, 2, 368.
34. For two recent reviews on inhibitors of glicosidases, see: (a) Asano, N. ; Nash, R. J.; Molyneux, R. J.; Fleet, G. W. J. Tetrahedron: Asymmetry 2000, 11, 1645. (b) Lillelund, V. H.; Jensen, H. H.; Liang, X.; Bols, M. Chem. Rev. 2002, 102, 515. Recent selected articles in this field: (c) Uchida, C.; Ogawa, S. Recent Res. Dev. Pure Appl. Chem. 1999, 3, 161. (d) Leroy, E.; Reymond, J.-L. Org. Lett. 1999, 1, 775. (e) Boss, O.; Leroy, E.; Blaser, A.; Reymond, J.-L. Org. Lett. 2000, 2, 151. (f) Kleban, M.; Hilgers, P.; Greul, J. N.; Kugler, R. D.; Li, Jing; P., Sylviane; V., Pierre; Jager, V. ChemBioChem 2001, 2, 365. (g) Greul, J. N.; Kleban, M.; Schneider, B.; Picasso, S.; Jager, V. ChemBioChem 2001, 2, 368.
35. Recent reviews: (a) Hughes, A. B.; Rudge, A. J. J. Nat. Prod. 1994, 57, 135. (b) Jacob, G. S. Curr. Opin. Struct. Biol. 1995, 5, 5. (c) Ganem, B. Acc. Chem. Res. 1996, 29, 340. (d) Bols, M. Acc. Chem. Res. 1998, 31, 1. (e) Heighten, T. D.; Vasella, A. T. Angew. Chem., Int. Ed. Engl. 1999, 38, 750. (f) Sears, P.; Wong, C.-H. Angew. Chem., Int. Ed. Engl. 1999, 38, 2300. (g) Berecibar, A.; Grandjean, C.; Siriwardena, A. Chem. Rev. 1999, 99, 779.
36. Recent reviews: (a) Hughes, A. B.; Rudge, A. J. J. Nat. Prod. 1994, 57, 135. (b) Jacob, G. S. Curr. Opin. Struct. Biol. 1995, 5, 5. (c) Ganem, B. Acc. Chem. Res. 1996, 29, 340. (d) Bols, M. Acc. Chem. Res. 1998, 31, 1. (e) Heighten, T. D.; Vasella, A. T. Angew. Chem., Int. Ed. Engl. 1999, 38, 750. (f) Sears, P.; Wong, C.-H. Angew. Chem., Int. Ed. Engl. 1999, 38, 2300. (g) Berecibar, A.; Grandjean, C.; Siriwardena, A. Chem. Rev. 1999, 99, 779.
37. Recent reviews: (a) Hughes, A. B.; Rudge, A. J. J. Nat. Prod. 1994, 57, 135. (b) Jacob, G. S. Curr. Opin. Struct. Biol. 1995, 5, 5. (c) Ganem, B. Acc. Chem. Res. 1996, 29, 340. (d) Bols, M. Acc. Chem. Res. 1998, 31, 1. (e) Heighten, T. D.; Vasella, A. T. Angew. Chem., Int. Ed. Engl. 1999, 38, 750. (f) Sears, P.; Wong, C.-H. Angew. Chem., Int. Ed. Engl. 1999, 38, 2300. (g) Berecibar, A.; Grandjean, C.; Siriwardena, A. Chem. Rev. 1999, 99, 779.
38. Recent reviews: (a) Hughes, A. B.; Rudge, A. J. J. Nat. Prod. 1994, 57, 135. (b) Jacob, G. S. Curr. Opin. Struct. Biol. 1995, 5, 5. (c) Ganem, B. Acc. Chem. Res. 1996, 29, 340. (d) Bols, M. Acc. Chem. Res. 1998, 31, 1. (e) Heighten, T. D.; Vasella, A. T. Angew. Chem., Int. Ed. Engl. 1999, 38, 750. (f) Sears, P.; Wong, C.-H. Angew. Chem., Int. Ed. Engl. 1999, 38, 2300. (g) Berecibar, A.; Grandjean, C.; Siriwardena, A. Chem. Rev. 1999, 99, 779.
39. Recent reviews: (a) Hughes, A. B.; Rudge, A. J. J. Nat. Prod. 1994, 57, 135. (b) Jacob, G. S. Curr. Opin. Struct. Biol. 1995, 5, 5. (c) Ganem, B. Acc. Chem. Res. 1996, 29, 340. (d) Bols, M. Acc. Chem. Res. 1998, 31, 1. (e) Heighten, T. D.; Vasella, A. T. Angew. Chem., Int. Ed. Engl. 1999, 38, 750. (f) Sears, P.; Wong, C.-H. Angew. Chem., Int. Ed. Engl. 1999, 38, 2300. (g) Berecibar, A.; Grandjean, C.; Siriwardena, A. Chem. Rev. 1999, 99, 779.
40. Recent reviews: (a) Hughes, A. B.; Rudge, A. J. J. Nat. Prod. 1994, 57, 135. (b) Jacob, G. S. Curr. Opin. Struct. Biol. 1995, 5, 5. (c) Ganem, B. Acc. Chem. Res. 1996, 29, 340. (d) Bols, M. Acc. Chem. Res. 1998, 31, 1. (e) Heighten, T. D.; Vasella, A. T. Angew. Chem., Int. Ed. Engl. 1999, 38, 750. (f) Sears, P.; Wong, C.-H. Angew. Chem., Int. Ed. Engl. 1999, 38, 2300. (g) Berecibar, A.; Grandjean, C.; Siriwardena, A. Chem. Rev. 1999, 99, 779.
41. Recent reviews: (a) Hughes, A. B.; Rudge, A. J. J. Nat. Prod. 1994, 57, 135. (b) Jacob, G. S. Curr. Opin. Struct. Biol. 1995, 5, 5. (c) Ganem, B. Acc. Chem. Res. 1996, 29, 340. (d) Bols, M. Acc. Chem. Res. 1998, 31, 1. (e) Heighten, T. D.; Vasella, A. T. Angew. Chem., Int. Ed. Engl. 1999, 38, 750. (f) Sears, P.; Wong, C.-H. Angew. Chem., Int. Ed. Engl. 1999, 38, 2300. (g) Berecibar, A.; Grandjean, C.; Siriwardena, A. Chem. Rev. 1999, 99, 779.
42. (a) Fairbanks, A. J.; Hui, A.; Skead, B. M.; de Q. Lilley, P. M.; Lamont, B.; Storer, R.; Saunders: J.; Watkin, D. J.; Fleet, G. W. J. Tetrahedron Lett. 1994, 35, 8891.
43. (b) Hui, A.; Fairbanks, A. J.; Nash, R. J.; de Q. Lilley, P. M.; Storer, R.; Watkin, D. J.; Fleet, G. W. J. Tetrahedron Lett. 1994, 35, 8895.
44. Compound 1 was easily prepared by ozonolysis of the corresponding azide, which was obtained from D-glucose, as per: Fleet, G. W. J.; Carpenter, N. M.; Petursson, S.; Ramsden, N. G. Tetrahedron Lett. 1990, 31, 409-412.
45. Fleet, G. W. J.; Ramsden, N. G.; Witty, D. R. Tetrahedron 1989, 45, 327.
46. Crystallographic data for the structure of compound 13 have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-205610. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, U.K. (fax (+44)1223-336-033; e-mail depositccdc.cam.ac.uk).