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See e.g.: (a) Casiraghi, G.; Zanardi, F. Chem. Rev. 1995, 95, 1677-1716; (b) Iminosugars as Glycosidase Inhibitors; Stütz, A. E., Ed.; Wiley-VCH: Weinheim, 1999; (c) Zeng, Y.; Pan, Y. T.; Asano, N.; Nash, R. J.; Elbein, A. D. Glycobiology 1997, 7, 297; (d) Asano, N.; Nash, R. J.; Molyneux, R. J. Fleet, G. W. Tetrahedron: Asymmetry 2000, 11, 1645-1680; (e) Lillelund, V. H.; Jensen, H. H.; Liang, X.; Bols. M. Chem. Rev. 2002, 102, 515-553.
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See e.g.: (a) Casiraghi, G.; Zanardi, F. Chem. Rev. 1995, 95, 1677-1716; (b) Iminosugars as Glycosidase Inhibitors; Stütz, A. E., Ed.; Wiley-VCH: Weinheim, 1999; (c) Zeng, Y.; Pan, Y. T.; Asano, N.; Nash, R. J.; Elbein, A. D. Glycobiology 1997, 7, 297; (d) Asano, N.; Nash, R. J.; Molyneux, R. J. Fleet, G. W. Tetrahedron: Asymmetry 2000, 11, 1645-1680; (e) Lillelund, V. H.; Jensen, H. H.; Liang, X.; Bols. M. Chem. Rev. 2002, 102, 515-553.
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See e.g.: (a) Casiraghi, G.; Zanardi, F. Chem. Rev. 1995, 95, 1677-1716; (b) Iminosugars as Glycosidase Inhibitors; Stütz, A. E., Ed.; Wiley-VCH: Weinheim, 1999; (c) Zeng, Y.; Pan, Y. T.; Asano, N.; Nash, R. J.; Elbein, A. D. Glycobiology 1997, 7, 297; (d) Asano, N.; Nash, R. J.; Molyneux, R. J. Fleet, G. W. Tetrahedron: Asymmetry 2000, 11, 1645-1680; (e) Lillelund, V. H.; Jensen, H. H.; Liang, X.; Bols. M. Chem. Rev. 2002, 102, 515-553.
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Zeng, Y.1
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Nash, R.J.4
Elbein, A.D.5
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0034607947
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See e.g.: (a) Casiraghi, G.; Zanardi, F. Chem. Rev. 1995, 95, 1677-1716; (b) Iminosugars as Glycosidase Inhibitors; Stütz, A. E., Ed.; Wiley-VCH: Weinheim, 1999; (c) Zeng, Y.; Pan, Y. T.; Asano, N.; Nash, R. J.; Elbein, A. D. Glycobiology 1997, 7, 297; (d) Asano, N.; Nash, R. J.; Molyneux, R. J. Fleet, G. W. Tetrahedron: Asymmetry 2000, 11, 1645-1680; (e) Lillelund, V. H.; Jensen, H. H.; Liang, X.; Bols. M. Chem. Rev. 2002, 102, 515-553.
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(2000)
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Asano, N.1
Nash, R.J.2
Molyneux, R.J.3
Fleet, G.W.4
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See e.g.: (a) Casiraghi, G.; Zanardi, F. Chem. Rev. 1995, 95, 1677-1716; (b) Iminosugars as Glycosidase Inhibitors; Stütz, A. E., Ed.; Wiley-VCH: Weinheim, 1999; (c) Zeng, Y.; Pan, Y. T.; Asano, N.; Nash, R. J.; Elbein, A. D. Glycobiology 1997, 7, 297; (d) Asano, N.; Nash, R. J.; Molyneux, R. J. Fleet, G. W. Tetrahedron: Asymmetry 2000, 11, 1645-1680; (e) Lillelund, V. H.; Jensen, H. H.; Liang, X.; Bols. M. Chem. Rev. 2002, 102, 515-553.
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Lillelund, V.H.1
Jensen, H.H.2
Liang, X.3
Bols, M.4
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See e.g.: (a) Goss, P. E.; Baker, M. A.; Carver, J. P.; Dennis, J. W. Clin. Cancer Res. 1995, 1, 935; (b) Das, P. C.; Robert, J. D.; White, S. L.; Olden, K. Oncol. Res. 1995, 7, 425.
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Goss, P.E.1
Baker, M.A.2
Carver, J.P.3
Dennis, J.W.4
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See e.g.: (a) Goss, P. E.; Baker, M. A.; Carver, J. P.; Dennis, J. W. Clin. Cancer Res. 1995, 1, 935; (b) Das, P. C.; Robert, J. D.; White, S. L.; Olden, K. Oncol. Res. 1995, 7, 425.
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, vol.7
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Das, P.C.1
Robert, J.D.2
White, S.L.3
Olden, K.4
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8
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84944647079
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Atta-ur-Rahman, Ed.; Elsevier: Amsterdam
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For reviews, see e.g.: (a) Cossy, J.; Vogel, P. Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1993; Vol. 12, pp. 275-363; (b) El Nemr, A. Tetrahedron 2000, 56, 8579-8629; (c) El Ashry, E. S. H.; Rahed, N.; Shobier, A. H. S. Pharmazie 2000, 55, 331-348.
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(1993)
Studies in Natural Products Chemistry
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, pp. 275-363
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Cossy, J.1
Vogel, P.2
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For reviews, see e.g.: (a) Cossy, J.; Vogel, P. Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1993; Vol. 12, pp. 275-363; (b) El Nemr, A. Tetrahedron 2000, 56, 8579-8629; (c) El Ashry, E. S. H.; Rahed, N.; Shobier, A. H. S. Pharmazie 2000, 55, 331-348.
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Tetrahedron
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, pp. 8579-8629
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El Nemr, A.1
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0034071690
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For reviews, see e.g.: (a) Cossy, J.; Vogel, P. Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1993; Vol. 12, pp. 275-363; (b) El Nemr, A. Tetrahedron 2000, 56, 8579-8629; (c) El Ashry, E. S. H.; Rahed, N.; Shobier, A. H. S. Pharmazie 2000, 55, 331-348.
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, vol.55
, pp. 331-348
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El Ashry, E.S.H.1
Rahed, N.2
Shobier, A.H.S.3
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See e.g.: lentiginosine and derivatives: (a) Brandi, A.; Cicchi, S.; Cordero, F. M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem. 1995, 60, 6806-6812; (b) Cardona, F.; Goti, A.; Picasso, S.; Vogel, P.; Brandi, A. J. Carbohydr. Chem. 2000, 19, 585-601; (c) pentahydroxyindolizidines: Chen, Y.; Vogel, P. J. Org. Chem. 1994, 59, 2487-2496; Picasso, S.; Chen, Y.; Vogel, P. Carbohydr. Lett. 1993, 1, 1-8; (d) Izquierdo, I.; Plaza, M. J.; Robles, R.; Mota, A. J. Tetrahedron: Asymmetry 1998, 9, 1015-1027; 5-azacastanospermine: (e) Søndergard, K.; Liang, X.; Bols, M. Chem. Eur. J. 2001, 7, 2324-2331.
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Brandi, A.1
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Frignoli, R.4
Goti, A.5
Picasso, S.6
Vogel, P.7
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0034364933
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See e.g.: lentiginosine and derivatives: (a) Brandi, A.; Cicchi, S.; Cordero, F. M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem. 1995, 60, 6806-6812; (b) Cardona, F.; Goti, A.; Picasso, S.; Vogel, P.; Brandi, A. J. Carbohydr. Chem. 2000, 19, 585-601; (c) pentahydroxyindolizidines: Chen, Y.; Vogel, P. J. Org. Chem. 1994, 59, 2487-2496; Picasso, S.; Chen, Y.; Vogel, P. Carbohydr. Lett. 1993, 1, 1-8; (d) Izquierdo, I.; Plaza, M. J.; Robles, R.; Mota, A. J. Tetrahedron: Asymmetry 1998, 9, 1015-1027; 5-azacastanospermine: (e) Søndergard, K.; Liang, X.; Bols, M. Chem. Eur. J. 2001, 7, 2324-2331.
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Goti, A.2
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Vogel, P.4
Brandi, A.5
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0028352612
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See e.g.: lentiginosine and derivatives: (a) Brandi, A.; Cicchi, S.; Cordero, F. M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem. 1995, 60, 6806-6812; (b) Cardona, F.; Goti, A.; Picasso, S.; Vogel, P.; Brandi, A. J. Carbohydr. Chem. 2000, 19, 585-601; (c) pentahydroxyindolizidines: Chen, Y.; Vogel, P. J. Org. Chem. 1994, 59, 2487-2496; Picasso, S.; Chen, Y.; Vogel, P. Carbohydr. Lett. 1993, 1, 1-8; (d) Izquierdo, I.; Plaza, M. J.; Robles, R.; Mota, A. J. Tetrahedron: Asymmetry 1998, 9, 1015-1027; 5-azacastanospermine: (e) Søndergard, K.; Liang, X.; Bols, M. Chem. Eur. J. 2001, 7, 2324-2331.
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Chen, Y.1
Vogel, P.2
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See e.g.: lentiginosine and derivatives: (a) Brandi, A.; Cicchi, S.; Cordero, F. M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem. 1995, 60, 6806-6812; (b) Cardona, F.; Goti, A.; Picasso, S.; Vogel, P.; Brandi, A. J. Carbohydr. Chem. 2000, 19, 585-601; (c) pentahydroxyindolizidines: Chen, Y.; Vogel, P. J. Org. Chem. 1994, 59, 2487-2496; Picasso, S.; Chen, Y.; Vogel, P. Carbohydr. Lett. 1993, 1, 1-8; (d) Izquierdo, I.; Plaza, M. J.; Robles, R.; Mota, A. J. Tetrahedron: Asymmetry 1998, 9, 1015-1027; 5-azacastanospermine: (e) Søndergard, K.; Liang, X.; Bols, M. Chem. Eur. J. 2001, 7, 2324-2331.
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Picasso, S.1
Chen, Y.2
Vogel, P.3
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See e.g.: lentiginosine and derivatives: (a) Brandi, A.; Cicchi, S.; Cordero, F. M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem. 1995, 60, 6806-6812; (b) Cardona, F.; Goti, A.; Picasso, S.; Vogel, P.; Brandi, A. J. Carbohydr. Chem. 2000, 19, 585-601; (c) pentahydroxyindolizidines: Chen, Y.; Vogel, P. J. Org. Chem. 1994, 59, 2487-2496; Picasso, S.; Chen, Y.; Vogel, P. Carbohydr. Lett. 1993, 1, 1-8; (d) Izquierdo, I.; Plaza, M. J.; Robles, R.; Mota, A. J. Tetrahedron: Asymmetry 1998, 9, 1015-1027; 5-azacastanospermine: (e) Søndergard, K.; Liang, X.; Bols, M. Chem. Eur. J. 2001, 7, 2324-2331.
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Tetrahedron: Asymmetry
, vol.9
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Izquierdo, I.1
Plaza, M.J.2
Robles, R.3
Mota, A.J.4
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16
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0035354691
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See e.g.: lentiginosine and derivatives: (a) Brandi, A.; Cicchi, S.; Cordero, F. M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem. 1995, 60, 6806-6812; (b) Cardona, F.; Goti, A.; Picasso, S.; Vogel, P.; Brandi, A. J. Carbohydr. Chem. 2000, 19, 585-601; (c) pentahydroxyindolizidines: Chen, Y.; Vogel, P. J. Org. Chem. 1994, 59, 2487-2496; Picasso, S.; Chen, Y.; Vogel, P. Carbohydr. Lett. 1993, 1, 1-8; (d) Izquierdo, I.; Plaza, M. J.; Robles, R.; Mota, A. J. Tetrahedron: Asymmetry 1998, 9, 1015-1027; 5-azacastanospermine: (e) Søndergard, K.; Liang, X.; Bols, M. Chem. Eur. J. 2001, 7, 2324-2331.
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Søndergard, K.1
Liang, X.2
Bols, M.3
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Kawakami T., Ohtake H., Arakawa H., Okachi T., Imada Y., Murahashi S.-I. Org. Lett. 1:1999;107-110.
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0030592842
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Davis B., Bell A.A., Nash R.J., Watson A.A., Griffiths R.C., Jones M.G., Smith C., Fleet G.W.J. Tetrahedron Lett. 37:1996;8565-8568.
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Davis, B.1
Bell, A.A.2
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Watson, A.A.4
Griffiths, R.C.5
Jones, M.G.6
Smith, C.7
Fleet, G.W.J.8
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25
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0005129784
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note
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3 was added and the mixture stirred for 30 min at rt and then extracted with AcOEt. The combined extracts were washed with brine and water, dried and evaporated. Purification was achieved by column chromatography with DCM:acetone 25:1 as eluant.
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27
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0005127830
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note
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1,8a=3.2, H-8a), 3.77 (d, 2H, H-6).
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29
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0005226441
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note
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2 (0.1 equiv.) was added. The reaction mixture was stirred at 0°C for x days (AD-mixα, x=1; AD-mixβ, x=2). Work-up procedure is as described for osmylation.
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30
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0005134107
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note
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8β,8a=1.2, H-8β).
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