A Synthesis of L-Vancosamine Derivatives from Non-Carbohydrate Precursors by a Short Sequence Based on the Marshall, McDonald, and Du Bois Reactions

Organic Letters

Volumn 5, Issue 21, 2003, Pages 3891-3893

  Parker, Kathlyn A ^a   Chang, Wonsuk ^a  

^a STONY BROOK UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALKYNOL; ALLENE DERIVATIVE; ALLENYL STANNATE; ANTIBIOTIC AGENT; CARBAMIC ACID DERIVATIVE; CARBOHYDRATE; CARBOHYDRATE DERIVATIVE; CARBON; ETHER DERIVATIVE; HYDROGEN; LACTALDEHYDE ETHER; METHYL GROUP; N,N DIMETHYLVANCOSAMINE GLYCAL; RHODIUM; SILANE DERIVATIVE; TUNGSTEN; UNCLASSIFIED DRUG; VANCOSAMINE;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL REACTION; DIASTEREOISOMER; DU BOIS REACTION; ISOMERISM; MARSHALL REACTION; MCDONALD REACTION; STEREOCHEMISTRY;

CATALYSIS; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; HEXOSAMINES; INDICATORS AND REAGENTS; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 0242712766     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035479p     Document Type: Article

References (58)

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15. Synthesis of vancosamine or its derivatives: (a) Thang, T. T.; Winternitz, F.; Olesker, A.; Lagrange, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1979, 153. (b) Dyong, I.; Friege, H. Chem. Ber. 1979, 112, 3273. (c) Thang, T. T.; Winternitz, F.; Olesker, A.; Lagrange, A.; Lukacs, G. Tetrahedron Lett. 1980, 21, 4495. (d) Ahmad, H. I.; Brimacombe, J. S.; Mengech, A. S.; Tucker, L. C. N. Carbohydr. Res. 1981, 93, 288. (e) Dyong, I.; Friege, H.; Luftmann, H.; Merten, H. Chem. Ber. 1981, 114, 2669. (f) Fronza, G.; Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G. Tetrahedron Lett. 1981, 22, 5073. (g) Brimacombe, J. S.; Mengech, A. S.; Rahman, K. M. M.; Tucker, L. C. N. Carbohydr. Res. 1982, 110, 207. (h) Fronza, G.; Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G. J. Carbohydr. Chem. 1983, 2, 225. (i) Hamada, Y.; Kawai, A.; Shioiri, T. Tetrahedron Lett. 1984, 25, 5413. (j) Hauser, F. M.; Ellenberger, S. R. J. Org. Chem. 1986, 51, 50. (k) Dyong, I.; Weigand, J.; Thiem, J. Liebigs Ann. Chem. 1986, 577. (l) Klemer, A.; Wilbers, H. Liebigs Ann. Chem. 1987, 815. (m) Hamada, Y.; Kawai, A.; Matsui, T.; Hara, O.; Shioiri, T. Tetrahedron 1990, 46, 4823. (n) Greven, R.; Jütten, P.; Scharf, H.-D. Carbohydr. Res. 1995, 275, 83. (o) Nicolaou, K. C.; Mitchell, H. J.; van Delft, F. L.; Rübsam, F.; Rodriguez, R. M. Angew. Chem., Int. Ed. 1998, 37, 1871. (p) Nicolaou, K. C.; Mitchell, J. J.; Jain, N. F.; Bando, T.; Hughes, R.; Winssinger, N.; Natarajan, S.; Koumbis, A. E. Chem. Eur. J. 1999, 5, 2648. (q) Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Vega, J. A. Angew. Chem., Int. Ed. 2000, 39, 2525. (r) Smith, G. R.; Giuliano, R. M. Carbohydr. Res. 2000, 323, 208. (s) Cutchins, W. W.; McDonald, F. E. Org. Lett. 2002, 4, 749.
16. Synthesis of vancosamine or its derivatives: (a) Thang, T. T.; Winternitz, F.; Olesker, A.; Lagrange, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1979, 153. (b) Dyong, I.; Friege, H. Chem. Ber. 1979, 112, 3273. (c) Thang, T. T.; Winternitz, F.; Olesker, A.; Lagrange, A.; Lukacs, G. Tetrahedron Lett. 1980, 21, 4495. (d) Ahmad, H. I.; Brimacombe, J. S.; Mengech, A. S.; Tucker, L. C. N. Carbohydr. Res. 1981, 93, 288. (e) Dyong, I.; Friege, H.; Luftmann, H.; Merten, H. Chem. Ber. 1981, 114, 2669. (f) Fronza, G.; Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G. Tetrahedron Lett. 1981, 22, 5073. (g) Brimacombe, J. S.; Mengech, A. S.; Rahman, K. M. M.; Tucker, L. C. N. Carbohydr. Res. 1982, 110, 207. (h) Fronza, G.; Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G. J. Carbohydr. Chem. 1983, 2, 225. (i) Hamada, Y.; Kawai, A.; Shioiri, T. Tetrahedron Lett. 1984, 25, 5413. (j) Hauser, F. M.; Ellenberger, S. R. J. Org. Chem. 1986, 51, 50. (k) Dyong, I.; Weigand, J.; Thiem, J. Liebigs Ann. Chem. 1986, 577. (l) Klemer, A.; Wilbers, H. Liebigs Ann. Chem. 1987, 815. (m) Hamada, Y.; Kawai, A.; Matsui, T.; Hara, O.; Shioiri, T. Tetrahedron 1990, 46, 4823. (n) Greven, R.; Jütten, P.; Scharf, H.-D. Carbohydr. Res. 1995, 275, 83. (o) Nicolaou, K. C.; Mitchell, H. J.; van Delft, F. L.; Rübsam, F.; Rodriguez, R. M. Angew. Chem., Int. Ed. 1998, 37, 1871. (p) Nicolaou, K. C.; Mitchell, J. J.; Jain, N. F.; Bando, T.; Hughes, R.; Winssinger, N.; Natarajan, S.; Koumbis, A. E. Chem. Eur. J. 1999, 5, 2648. (q) Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Vega, J. A. Angew. Chem., Int. Ed. 2000, 39, 2525. (r) Smith, G. R.; Giuliano, R. M. Carbohydr. Res. 2000, 323, 208. (s) Cutchins, W. W.; McDonald, F. E. Org. Lett. 2002, 4, 749.
17. Synthesis of vancosamine or its derivatives: (a) Thang, T. T.; Winternitz, F.; Olesker, A.; Lagrange, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1979, 153. (b) Dyong, I.; Friege, H. Chem. Ber. 1979, 112, 3273. (c) Thang, T. T.; Winternitz, F.; Olesker, A.; Lagrange, A.; Lukacs, G. Tetrahedron Lett. 1980, 21, 4495. (d) Ahmad, H. I.; Brimacombe, J. S.; Mengech, A. S.; Tucker, L. C. N. Carbohydr. Res. 1981, 93, 288. (e) Dyong, I.; Friege, H.; Luftmann, H.; Merten, H. Chem. Ber. 1981, 114, 2669. (f) Fronza, G.; Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G. Tetrahedron Lett. 1981, 22, 5073. (g) Brimacombe, J. S.; Mengech, A. S.; Rahman, K. M. M.; Tucker, L. C. N. Carbohydr. Res. 1982, 110, 207. (h) Fronza, G.; Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G. J. Carbohydr. Chem. 1983, 2, 225. (i) Hamada, Y.; Kawai, A.; Shioiri, T. Tetrahedron Lett. 1984, 25, 5413. (j) Hauser, F. M.; Ellenberger, S. R. J. Org. Chem. 1986, 51, 50. (k) Dyong, I.; Weigand, J.; Thiem, J. Liebigs Ann. Chem. 1986, 577. (l) Klemer, A.; Wilbers, H. Liebigs Ann. Chem. 1987, 815. (m) Hamada, Y.; Kawai, A.; Matsui, T.; Hara, O.; Shioiri, T. Tetrahedron 1990, 46, 4823. (n) Greven, R.; Jütten, P.; Scharf, H.-D. Carbohydr. Res. 1995, 275, 83. (o) Nicolaou, K. C.; Mitchell, H. J.; van Delft, F. L.; Rübsam, F.; Rodriguez, R. M. Angew. Chem., Int. Ed. 1998, 37, 1871. (p) Nicolaou, K. C.; Mitchell, J. J.; Jain, N. F.; Bando, T.; Hughes, R.; Winssinger, N.; Natarajan, S.; Koumbis, A. E. Chem. Eur. J. 1999, 5, 2648. (q) Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Vega, J. A. Angew. Chem., Int. Ed. 2000, 39, 2525. (r) Smith, G. R.; Giuliano, R. M. Carbohydr. Res. 2000, 323, 208. (s) Cutchins, W. W.; McDonald, F. E. Org. Lett. 2002, 4, 749.
18. Synthesis of vancosamine or its derivatives: (a) Thang, T. T.; Winternitz, F.; Olesker, A.; Lagrange, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1979, 153. (b) Dyong, I.; Friege, H. Chem. Ber. 1979, 112, 3273. (c) Thang, T. T.; Winternitz, F.; Olesker, A.; Lagrange, A.; Lukacs, G. Tetrahedron Lett. 1980, 21, 4495. (d) Ahmad, H. I.; Brimacombe, J. S.; Mengech, A. S.; Tucker, L. C. N. Carbohydr. Res. 1981, 93, 288. (e) Dyong, I.; Friege, H.; Luftmann, H.; Merten, H. Chem. Ber. 1981, 114, 2669. (f) Fronza, G.; Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G. Tetrahedron Lett. 1981, 22, 5073. (g) Brimacombe, J. S.; Mengech, A. S.; Rahman, K. M. M.; Tucker, L. C. N. Carbohydr. Res. 1982, 110, 207. (h) Fronza, G.; Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G. J. Carbohydr. Chem. 1983, 2, 225. (i) Hamada, Y.; Kawai, A.; Shioiri, T. Tetrahedron Lett. 1984, 25, 5413. (j) Hauser, F. M.; Ellenberger, S. R. J. Org. Chem. 1986, 51, 50. (k) Dyong, I.; Weigand, J.; Thiem, J. Liebigs Ann. Chem. 1986, 577. (l) Klemer, A.; Wilbers, H. Liebigs Ann. Chem. 1987, 815. (m) Hamada, Y.; Kawai, A.; Matsui, T.; Hara, O.; Shioiri, T. Tetrahedron 1990, 46, 4823. (n) Greven, R.; Jütten, P.; Scharf, H.-D. Carbohydr. Res. 1995, 275, 83. (o) Nicolaou, K. C.; Mitchell, H. J.; van Delft, F. L.; Rübsam, F.; Rodriguez, R. M. Angew. Chem., Int. Ed. 1998, 37, 1871. (p) Nicolaou, K. C.; Mitchell, J. J.; Jain, N. F.; Bando, T.; Hughes, R.; Winssinger, N.; Natarajan, S.; Koumbis, A. E. Chem. Eur. J. 1999, 5, 2648. (q) Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Vega, J. A. Angew. Chem., Int. Ed. 2000, 39, 2525. (r) Smith, G. R.; Giuliano, R. M. Carbohydr. Res. 2000, 323, 208. (s) Cutchins, W. W.; McDonald, F. E. Org. Lett. 2002, 4, 749.
19. Synthesis of vancosamine or its derivatives: (a) Thang, T. T.; Winternitz, F.; Olesker, A.; Lagrange, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1979, 153. (b) Dyong, I.; Friege, H. Chem. Ber. 1979, 112, 3273. (c) Thang, T. T.; Winternitz, F.; Olesker, A.; Lagrange, A.; Lukacs, G. Tetrahedron Lett. 1980, 21, 4495. (d) Ahmad, H. I.; Brimacombe, J. S.; Mengech, A. S.; Tucker, L. C. N. Carbohydr. Res. 1981, 93, 288. (e) Dyong, I.; Friege, H.; Luftmann, H.; Merten, H. Chem. Ber. 1981, 114, 2669. (f) Fronza, G.; Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G. Tetrahedron Lett. 1981, 22, 5073. (g) Brimacombe, J. S.; Mengech, A. S.; Rahman, K. M. M.; Tucker, L. C. N. Carbohydr. Res. 1982, 110, 207. (h) Fronza, G.; Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G. J. Carbohydr. Chem. 1983, 2, 225. (i) Hamada, Y.; Kawai, A.; Shioiri, T. Tetrahedron Lett. 1984, 25, 5413. (j) Hauser, F. M.; Ellenberger, S. R. J. Org. Chem. 1986, 51, 50. (k) Dyong, I.; Weigand, J.; Thiem, J. Liebigs Ann. Chem. 1986, 577. (l) Klemer, A.; Wilbers, H. Liebigs Ann. Chem. 1987, 815. (m) Hamada, Y.; Kawai, A.; Matsui, T.; Hara, O.; Shioiri, T. Tetrahedron 1990, 46, 4823. (n) Greven, R.; Jütten, P.; Scharf, H.-D. Carbohydr. Res. 1995, 275, 83. (o) Nicolaou, K. C.; Mitchell, H. J.; van Delft, F. L.; Rübsam, F.; Rodriguez, R. M. Angew. Chem., Int. Ed. 1998, 37, 1871. (p) Nicolaou, K. C.; Mitchell, J. J.; Jain, N. F.; Bando, T.; Hughes, R.; Winssinger, N.; Natarajan, S.; Koumbis, A. E. Chem. Eur. J. 1999, 5, 2648. (q) Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Vega, J. A. Angew. Chem., Int. Ed. 2000, 39, 2525. (r) Smith, G. R.; Giuliano, R. M. Carbohydr. Res. 2000, 323, 208. (s) Cutchins, W. W.; McDonald, F. E. Org. Lett. 2002, 4, 749.
20. Synthesis of vancosamine or its derivatives: (a) Thang, T. T.; Winternitz, F.; Olesker, A.; Lagrange, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1979, 153. (b) Dyong, I.; Friege, H. Chem. Ber. 1979, 112, 3273. (c) Thang, T. T.; Winternitz, F.; Olesker, A.; Lagrange, A.; Lukacs, G. Tetrahedron Lett. 1980, 21, 4495. (d) Ahmad, H. I.; Brimacombe, J. S.; Mengech, A. S.; Tucker, L. C. N. Carbohydr. Res. 1981, 93, 288. (e) Dyong, I.; Friege, H.; Luftmann, H.; Merten, H. Chem. Ber. 1981, 114, 2669. (f) Fronza, G.; Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G. Tetrahedron Lett. 1981, 22, 5073. (g) Brimacombe, J. S.; Mengech, A. S.; Rahman, K. M. M.; Tucker, L. C. N. Carbohydr. Res. 1982, 110, 207. (h) Fronza, G.; Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G. J. Carbohydr. Chem. 1983, 2, 225. (i) Hamada, Y.; Kawai, A.; Shioiri, T. Tetrahedron Lett. 1984, 25, 5413. (j) Hauser, F. M.; Ellenberger, S. R. J. Org. Chem. 1986, 51, 50. (k) Dyong, I.; Weigand, J.; Thiem, J. Liebigs Ann. Chem. 1986, 577. (l) Klemer, A.; Wilbers, H. Liebigs Ann. Chem. 1987, 815. (m) Hamada, Y.; Kawai, A.; Matsui, T.; Hara, O.; Shioiri, T. Tetrahedron 1990, 46, 4823. (n) Greven, R.; Jütten, P.; Scharf, H.-D. Carbohydr. Res. 1995, 275, 83. (o) Nicolaou, K. C.; Mitchell, H. J.; van Delft, F. L.; Rübsam, F.; Rodriguez, R. M. Angew. Chem., Int. Ed. 1998, 37, 1871. (p) Nicolaou, K. C.; Mitchell, J. J.; Jain, N. F.; Bando, T.; Hughes, R.; Winssinger, N.; Natarajan, S.; Koumbis, A. E. Chem. Eur. J. 1999, 5, 2648. (q) Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Vega, J. A. Angew. Chem., Int. Ed. 2000, 39, 2525. (r) Smith, G. R.; Giuliano, R. M. Carbohydr. Res. 2000, 323, 208. (s) Cutchins, W. W.; McDonald, F. E. Org. Lett. 2002, 4, 749.
21. Synthesis of vancosamine or its derivatives: (a) Thang, T. T.; Winternitz, F.; Olesker, A.; Lagrange, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1979, 153. (b) Dyong, I.; Friege, H. Chem. Ber. 1979, 112, 3273. (c) Thang, T. T.; Winternitz, F.; Olesker, A.; Lagrange, A.; Lukacs, G. Tetrahedron Lett. 1980, 21, 4495. (d) Ahmad, H. I.; Brimacombe, J. S.; Mengech, A. S.; Tucker, L. C. N. Carbohydr. Res. 1981, 93, 288. (e) Dyong, I.; Friege, H.; Luftmann, H.; Merten, H. Chem. Ber. 1981, 114, 2669. (f) Fronza, G.; Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G. Tetrahedron Lett. 1981, 22, 5073. (g) Brimacombe, J. S.; Mengech, A. S.; Rahman, K. M. M.; Tucker, L. C. N. Carbohydr. Res. 1982, 110, 207. (h) Fronza, G.; Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G. J. Carbohydr. Chem. 1983, 2, 225. (i) Hamada, Y.; Kawai, A.; Shioiri, T. Tetrahedron Lett. 1984, 25, 5413. (j) Hauser, F. M.; Ellenberger, S. R. J. Org. Chem. 1986, 51, 50. (k) Dyong, I.; Weigand, J.; Thiem, J. Liebigs Ann. Chem. 1986, 577. (l) Klemer, A.; Wilbers, H. Liebigs Ann. Chem. 1987, 815. (m) Hamada, Y.; Kawai, A.; Matsui, T.; Hara, O.; Shioiri, T. Tetrahedron 1990, 46, 4823. (n) Greven, R.; Jütten, P.; Scharf, H.-D. Carbohydr. Res. 1995, 275, 83. (o) Nicolaou, K. C.; Mitchell, H. J.; van Delft, F. L.; Rübsam, F.; Rodriguez, R. M. Angew. Chem., Int. Ed. 1998, 37, 1871. (p) Nicolaou, K. C.; Mitchell, J. J.; Jain, N. F.; Bando, T.; Hughes, R.; Winssinger, N.; Natarajan, S.; Koumbis, A. E. Chem. Eur. J. 1999, 5, 2648. (q) Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Vega, J. A. Angew. Chem., Int. Ed. 2000, 39, 2525. (r) Smith, G. R.; Giuliano, R. M. Carbohydr. Res. 2000, 323, 208. (s) Cutchins, W. W.; McDonald, F. E. Org. Lett. 2002, 4, 749.
22. Synthesis of vancosamine or its derivatives: (a) Thang, T. T.; Winternitz, F.; Olesker, A.; Lagrange, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1979, 153. (b) Dyong, I.; Friege, H. Chem. Ber. 1979, 112, 3273. (c) Thang, T. T.; Winternitz, F.; Olesker, A.; Lagrange, A.; Lukacs, G. Tetrahedron Lett. 1980, 21, 4495. (d) Ahmad, H. I.; Brimacombe, J. S.; Mengech, A. S.; Tucker, L. C. N. Carbohydr. Res. 1981, 93, 288. (e) Dyong, I.; Friege, H.; Luftmann, H.; Merten, H. Chem. Ber. 1981, 114, 2669. (f) Fronza, G.; Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G. Tetrahedron Lett. 1981, 22, 5073. (g) Brimacombe, J. S.; Mengech, A. S.; Rahman, K. M. M.; Tucker, L. C. N. Carbohydr. Res. 1982, 110, 207. (h) Fronza, G.; Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G. J. Carbohydr. Chem. 1983, 2, 225. (i) Hamada, Y.; Kawai, A.; Shioiri, T. Tetrahedron Lett. 1984, 25, 5413. (j) Hauser, F. M.; Ellenberger, S. R. J. Org. Chem. 1986, 51, 50. (k) Dyong, I.; Weigand, J.; Thiem, J. Liebigs Ann. Chem. 1986, 577. (l) Klemer, A.; Wilbers, H. Liebigs Ann. Chem. 1987, 815. (m) Hamada, Y.; Kawai, A.; Matsui, T.; Hara, O.; Shioiri, T. Tetrahedron 1990, 46, 4823. (n) Greven, R.; Jütten, P.; Scharf, H.-D. Carbohydr. Res. 1995, 275, 83. (o) Nicolaou, K. C.; Mitchell, H. J.; van Delft, F. L.; Rübsam, F.; Rodriguez, R. M. Angew. Chem., Int. Ed. 1998, 37, 1871. (p) Nicolaou, K. C.; Mitchell, J. J.; Jain, N. F.; Bando, T.; Hughes, R.; Winssinger, N.; Natarajan, S.; Koumbis, A. E. Chem. Eur. J. 1999, 5, 2648. (q) Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Vega, J. A. Angew. Chem., Int. Ed. 2000, 39, 2525. (r) Smith, G. R.; Giuliano, R. M. Carbohydr. Res. 2000, 323, 208. (s) Cutchins, W. W.; McDonald, F. E. Org. Lett. 2002, 4, 749.
23. Synthesis of vancosamine or its derivatives: (a) Thang, T. T.; Winternitz, F.; Olesker, A.; Lagrange, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1979, 153. (b) Dyong, I.; Friege, H. Chem. Ber. 1979, 112, 3273. (c) Thang, T. T.; Winternitz, F.; Olesker, A.; Lagrange, A.; Lukacs, G. Tetrahedron Lett. 1980, 21, 4495. (d) Ahmad, H. I.; Brimacombe, J. S.; Mengech, A. S.; Tucker, L. C. N. Carbohydr. Res. 1981, 93, 288. (e) Dyong, I.; Friege, H.; Luftmann, H.; Merten, H. Chem. Ber. 1981, 114, 2669. (f) Fronza, G.; Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G. Tetrahedron Lett. 1981, 22, 5073. (g) Brimacombe, J. S.; Mengech, A. S.; Rahman, K. M. M.; Tucker, L. C. N. Carbohydr. Res. 1982, 110, 207. (h) Fronza, G.; Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G. J. Carbohydr. Chem. 1983, 2, 225. (i) Hamada, Y.; Kawai, A.; Shioiri, T. Tetrahedron Lett. 1984, 25, 5413. (j) Hauser, F. M.; Ellenberger, S. R. J. Org. Chem. 1986, 51, 50. (k) Dyong, I.; Weigand, J.; Thiem, J. Liebigs Ann. Chem. 1986, 577. (l) Klemer, A.; Wilbers, H. Liebigs Ann. Chem. 1987, 815. (m) Hamada, Y.; Kawai, A.; Matsui, T.; Hara, O.; Shioiri, T. Tetrahedron 1990, 46, 4823. (n) Greven, R.; Jütten, P.; Scharf, H.-D. Carbohydr. Res. 1995, 275, 83. (o) Nicolaou, K. C.; Mitchell, H. J.; van Delft, F. L.; Rübsam, F.; Rodriguez, R. M. Angew. Chem., Int. Ed. 1998, 37, 1871. (p) Nicolaou, K. C.; Mitchell, J. J.; Jain, N. F.; Bando, T.; Hughes, R.; Winssinger, N.; Natarajan, S.; Koumbis, A. E. Chem. Eur. J. 1999, 5, 2648. (q) Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Vega, J. A. Angew. Chem., Int. Ed. 2000, 39, 2525. (r) Smith, G. R.; Giuliano, R. M. Carbohydr. Res. 2000, 323, 208. (s) Cutchins, W. W.; McDonald, F. E. Org. Lett. 2002, 4, 749.
24. Synthesis of vancosamine or its derivatives: (a) Thang, T. T.; Winternitz, F.; Olesker, A.; Lagrange, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1979, 153. (b) Dyong, I.; Friege, H. Chem. Ber. 1979, 112, 3273. (c) Thang, T. T.; Winternitz, F.; Olesker, A.; Lagrange, A.; Lukacs, G. Tetrahedron Lett. 1980, 21, 4495. (d) Ahmad, H. I.; Brimacombe, J. S.; Mengech, A. S.; Tucker, L. C. N. Carbohydr. Res. 1981, 93, 288. (e) Dyong, I.; Friege, H.; Luftmann, H.; Merten, H. Chem. Ber. 1981, 114, 2669. (f) Fronza, G.; Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G. Tetrahedron Lett. 1981, 22, 5073. (g) Brimacombe, J. S.; Mengech, A. S.; Rahman, K. M. M.; Tucker, L. C. N. Carbohydr. Res. 1982, 110, 207. (h) Fronza, G.; Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G. J. Carbohydr. Chem. 1983, 2, 225. (i) Hamada, Y.; Kawai, A.; Shioiri, T. Tetrahedron Lett. 1984, 25, 5413. (j) Hauser, F. M.; Ellenberger, S. R. J. Org. Chem. 1986, 51, 50. (k) Dyong, I.; Weigand, J.; Thiem, J. Liebigs Ann. Chem. 1986, 577. (l) Klemer, A.; Wilbers, H. Liebigs Ann. Chem. 1987, 815. (m) Hamada, Y.; Kawai, A.; Matsui, T.; Hara, O.; Shioiri, T. Tetrahedron 1990, 46, 4823. (n) Greven, R.; Jütten, P.; Scharf, H.-D. Carbohydr. Res. 1995, 275, 83. (o) Nicolaou, K. C.; Mitchell, H. J.; van Delft, F. L.; Rübsam, F.; Rodriguez, R. M. Angew. Chem., Int. Ed. 1998, 37, 1871. (p) Nicolaou, K. C.; Mitchell, J. J.; Jain, N. F.; Bando, T.; Hughes, R.; Winssinger, N.; Natarajan, S.; Koumbis, A. E. Chem. Eur. J. 1999, 5, 2648. (q) Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Vega, J. A. Angew. Chem., Int. Ed. 2000, 39, 2525. (r) Smith, G. R.; Giuliano, R. M. Carbohydr. Res. 2000, 323, 208. (s) Cutchins, W. W.; McDonald, F. E. Org. Lett. 2002, 4, 749.
25. Synthesis of vancosamine or its derivatives: (a) Thang, T. T.; Winternitz, F.; Olesker, A.; Lagrange, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1979, 153. (b) Dyong, I.; Friege, H. Chem. Ber. 1979, 112, 3273. (c) Thang, T. T.; Winternitz, F.; Olesker, A.; Lagrange, A.; Lukacs, G. Tetrahedron Lett. 1980, 21, 4495. (d) Ahmad, H. I.; Brimacombe, J. S.; Mengech, A. S.; Tucker, L. C. N. Carbohydr. Res. 1981, 93, 288. (e) Dyong, I.; Friege, H.; Luftmann, H.; Merten, H. Chem. Ber. 1981, 114, 2669. (f) Fronza, G.; Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G. Tetrahedron Lett. 1981, 22, 5073. (g) Brimacombe, J. S.; Mengech, A. S.; Rahman, K. M. M.; Tucker, L. C. N. Carbohydr. Res. 1982, 110, 207. (h) Fronza, G.; Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G. J. Carbohydr. Chem. 1983, 2, 225. (i) Hamada, Y.; Kawai, A.; Shioiri, T. Tetrahedron Lett. 1984, 25, 5413. (j) Hauser, F. M.; Ellenberger, S. R. J. Org. Chem. 1986, 51, 50. (k) Dyong, I.; Weigand, J.; Thiem, J. Liebigs Ann. Chem. 1986, 577. (l) Klemer, A.; Wilbers, H. Liebigs Ann. Chem. 1987, 815. (m) Hamada, Y.; Kawai, A.; Matsui, T.; Hara, O.; Shioiri, T. Tetrahedron 1990, 46, 4823. (n) Greven, R.; Jütten, P.; Scharf, H.-D. Carbohydr. Res. 1995, 275, 83. (o) Nicolaou, K. C.; Mitchell, H. J.; van Delft, F. L.; Rübsam, F.; Rodriguez, R. M. Angew. Chem., Int. Ed. 1998, 37, 1871. (p) Nicolaou, K. C.; Mitchell, J. J.; Jain, N. F.; Bando, T.; Hughes, R.; Winssinger, N.; Natarajan, S.; Koumbis, A. E. Chem. Eur. J. 1999, 5, 2648. (q) Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Vega, J. A. Angew. Chem., Int. Ed. 2000, 39, 2525. (r) Smith, G. R.; Giuliano, R. M. Carbohydr. Res. 2000, 323, 208. (s) Cutchins, W. W.; McDonald, F. E. Org. Lett. 2002, 4, 749.
26. Synthesis of vancosamine or its derivatives: (a) Thang, T. T.; Winternitz, F.; Olesker, A.; Lagrange, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1979, 153. (b) Dyong, I.; Friege, H. Chem. Ber. 1979, 112, 3273. (c) Thang, T. T.; Winternitz, F.; Olesker, A.; Lagrange, A.; Lukacs, G. Tetrahedron Lett. 1980, 21, 4495. (d) Ahmad, H. I.; Brimacombe, J. S.; Mengech, A. S.; Tucker, L. C. N. Carbohydr. Res. 1981, 93, 288. (e) Dyong, I.; Friege, H.; Luftmann, H.; Merten, H. Chem. Ber. 1981, 114, 2669. (f) Fronza, G.; Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G. Tetrahedron Lett. 1981, 22, 5073. (g) Brimacombe, J. S.; Mengech, A. S.; Rahman, K. M. M.; Tucker, L. C. N. Carbohydr. Res. 1982, 110, 207. (h) Fronza, G.; Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G. J. Carbohydr. Chem. 1983, 2, 225. (i) Hamada, Y.; Kawai, A.; Shioiri, T. Tetrahedron Lett. 1984, 25, 5413. (j) Hauser, F. M.; Ellenberger, S. R. J. Org. Chem. 1986, 51, 50. (k) Dyong, I.; Weigand, J.; Thiem, J. Liebigs Ann. Chem. 1986, 577. (l) Klemer, A.; Wilbers, H. Liebigs Ann. Chem. 1987, 815. (m) Hamada, Y.; Kawai, A.; Matsui, T.; Hara, O.; Shioiri, T. Tetrahedron 1990, 46, 4823. (n) Greven, R.; Jütten, P.; Scharf, H.-D. Carbohydr. Res. 1995, 275, 83. (o) Nicolaou, K. C.; Mitchell, H. J.; van Delft, F. L.; Rübsam, F.; Rodriguez, R. M. Angew. Chem., Int. Ed. 1998, 37, 1871. (p) Nicolaou, K. C.; Mitchell, J. J.; Jain, N. F.; Bando, T.; Hughes, R.; Winssinger, N.; Natarajan, S.; Koumbis, A. E. Chem. Eur. J. 1999, 5, 2648. (q) Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Vega, J. A. Angew. Chem., Int. Ed. 2000, 39, 2525. (r) Smith, G. R.; Giuliano, R. M. Carbohydr. Res. 2000, 323, 208. (s) Cutchins, W. W.; McDonald, F. E. Org. Lett. 2002, 4, 749.
27. Synthesis of vancosamine or its derivatives: (a) Thang, T. T.; Winternitz, F.; Olesker, A.; Lagrange, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1979, 153. (b) Dyong, I.; Friege, H. Chem. Ber. 1979, 112, 3273. (c) Thang, T. T.; Winternitz, F.; Olesker, A.; Lagrange, A.; Lukacs, G. Tetrahedron Lett. 1980, 21, 4495. (d) Ahmad, H. I.; Brimacombe, J. S.; Mengech, A. S.; Tucker, L. C. N. Carbohydr. Res. 1981, 93, 288. (e) Dyong, I.; Friege, H.; Luftmann, H.; Merten, H. Chem. Ber. 1981, 114, 2669. (f) Fronza, G.; Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G. Tetrahedron Lett. 1981, 22, 5073. (g) Brimacombe, J. S.; Mengech, A. S.; Rahman, K. M. M.; Tucker, L. C. N. Carbohydr. Res. 1982, 110, 207. (h) Fronza, G.; Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G. J. Carbohydr. Chem. 1983, 2, 225. (i) Hamada, Y.; Kawai, A.; Shioiri, T. Tetrahedron Lett. 1984, 25, 5413. (j) Hauser, F. M.; Ellenberger, S. R. J. Org. Chem. 1986, 51, 50. (k) Dyong, I.; Weigand, J.; Thiem, J. Liebigs Ann. Chem. 1986, 577. (l) Klemer, A.; Wilbers, H. Liebigs Ann. Chem. 1987, 815. (m) Hamada, Y.; Kawai, A.; Matsui, T.; Hara, O.; Shioiri, T. Tetrahedron 1990, 46, 4823. (n) Greven, R.; Jütten, P.; Scharf, H.-D. Carbohydr. Res. 1995, 275, 83. (o) Nicolaou, K. C.; Mitchell, H. J.; van Delft, F. L.; Rübsam, F.; Rodriguez, R. M. Angew. Chem., Int. Ed. 1998, 37, 1871. (p) Nicolaou, K. C.; Mitchell, J. J.; Jain, N. F.; Bando, T.; Hughes, R.; Winssinger, N.; Natarajan, S.; Koumbis, A. E. Chem. Eur. J. 1999, 5, 2648. (q) Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Vega, J. A. Angew. Chem., Int. Ed. 2000, 39, 2525. (r) Smith, G. R.; Giuliano, R. M. Carbohydr. Res. 2000, 323, 208. (s) Cutchins, W. W.; McDonald, F. E. Org. Lett. 2002, 4, 749.
28. Synthesis of vancosamine or its derivatives: (a) Thang, T. T.; Winternitz, F.; Olesker, A.; Lagrange, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1979, 153. (b) Dyong, I.; Friege, H. Chem. Ber. 1979, 112, 3273. (c) Thang, T. T.; Winternitz, F.; Olesker, A.; Lagrange, A.; Lukacs, G. Tetrahedron Lett. 1980, 21, 4495. (d) Ahmad, H. I.; Brimacombe, J. S.; Mengech, A. S.; Tucker, L. C. N. Carbohydr. Res. 1981, 93, 288. (e) Dyong, I.; Friege, H.; Luftmann, H.; Merten, H. Chem. Ber. 1981, 114, 2669. (f) Fronza, G.; Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G. Tetrahedron Lett. 1981, 22, 5073. (g) Brimacombe, J. S.; Mengech, A. S.; Rahman, K. M. M.; Tucker, L. C. N. Carbohydr. Res. 1982, 110, 207. (h) Fronza, G.; Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G. J. Carbohydr. Chem. 1983, 2, 225. (i) Hamada, Y.; Kawai, A.; Shioiri, T. Tetrahedron Lett. 1984, 25, 5413. (j) Hauser, F. M.; Ellenberger, S. R. J. Org. Chem. 1986, 51, 50. (k) Dyong, I.; Weigand, J.; Thiem, J. Liebigs Ann. Chem. 1986, 577. (l) Klemer, A.; Wilbers, H. Liebigs Ann. Chem. 1987, 815. (m) Hamada, Y.; Kawai, A.; Matsui, T.; Hara, O.; Shioiri, T. Tetrahedron 1990, 46, 4823. (n) Greven, R.; Jütten, P.; Scharf, H.-D. Carbohydr. Res. 1995, 275, 83. (o) Nicolaou, K. C.; Mitchell, H. J.; van Delft, F. L.; Rübsam, F.; Rodriguez, R. M. Angew. Chem., Int. Ed. 1998, 37, 1871. (p) Nicolaou, K. C.; Mitchell, J. J.; Jain, N. F.; Bando, T.; Hughes, R.; Winssinger, N.; Natarajan, S.; Koumbis, A. E. Chem. Eur. J. 1999, 5, 2648. (q) Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Vega, J. A. Angew. Chem., Int. Ed. 2000, 39, 2525. (r) Smith, G. R.; Giuliano, R. M. Carbohydr. Res. 2000, 323, 208. (s) Cutchins, W. W.; McDonald, F. E. Org. Lett. 2002, 4, 749.
29. Synthesis of vancosamine or its derivatives: (a) Thang, T. T.; Winternitz, F.; Olesker, A.; Lagrange, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1979, 153. (b) Dyong, I.; Friege, H. Chem. Ber. 1979, 112, 3273. (c) Thang, T. T.; Winternitz, F.; Olesker, A.; Lagrange, A.; Lukacs, G. Tetrahedron Lett. 1980, 21, 4495. (d) Ahmad, H. I.; Brimacombe, J. S.; Mengech, A. S.; Tucker, L. C. N. Carbohydr. Res. 1981, 93, 288. (e) Dyong, I.; Friege, H.; Luftmann, H.; Merten, H. Chem. Ber. 1981, 114, 2669. (f) Fronza, G.; Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G. Tetrahedron Lett. 1981, 22, 5073. (g) Brimacombe, J. S.; Mengech, A. S.; Rahman, K. M. M.; Tucker, L. C. N. Carbohydr. Res. 1982, 110, 207. (h) Fronza, G.; Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G. J. Carbohydr. Chem. 1983, 2, 225. (i) Hamada, Y.; Kawai, A.; Shioiri, T. Tetrahedron Lett. 1984, 25, 5413. (j) Hauser, F. M.; Ellenberger, S. R. J. Org. Chem. 1986, 51, 50. (k) Dyong, I.; Weigand, J.; Thiem, J. Liebigs Ann. Chem. 1986, 577. (l) Klemer, A.; Wilbers, H. Liebigs Ann. Chem. 1987, 815. (m) Hamada, Y.; Kawai, A.; Matsui, T.; Hara, O.; Shioiri, T. Tetrahedron 1990, 46, 4823. (n) Greven, R.; Jütten, P.; Scharf, H.-D. Carbohydr. Res. 1995, 275, 83. (o) Nicolaou, K. C.; Mitchell, H. J.; van Delft, F. L.; Rübsam, F.; Rodriguez, R. M. Angew. Chem., Int. Ed. 1998, 37, 1871. (p) Nicolaou, K. C.; Mitchell, J. J.; Jain, N. F.; Bando, T.; Hughes, R.; Winssinger, N.; Natarajan, S.; Koumbis, A. E. Chem. Eur. J. 1999, 5, 2648. (q) Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Vega, J. A. Angew. Chem., Int. Ed. 2000, 39, 2525. (r) Smith, G. R.; Giuliano, R. M. Carbohydr. Res. 2000, 323, 208. (s) Cutchins, W. W.; McDonald, F. E. Org. Lett. 2002, 4, 749.
30. Synthesis of vancosamine or its derivatives: (a) Thang, T. T.; Winternitz, F.; Olesker, A.; Lagrange, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1979, 153. (b) Dyong, I.; Friege, H. Chem. Ber. 1979, 112, 3273. (c) Thang, T. T.; Winternitz, F.; Olesker, A.; Lagrange, A.; Lukacs, G. Tetrahedron Lett. 1980, 21, 4495. (d) Ahmad, H. I.; Brimacombe, J. S.; Mengech, A. S.; Tucker, L. C. N. Carbohydr. Res. 1981, 93, 288. (e) Dyong, I.; Friege, H.; Luftmann, H.; Merten, H. Chem. Ber. 1981, 114, 2669. (f) Fronza, G.; Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G. Tetrahedron Lett. 1981, 22, 5073. (g) Brimacombe, J. S.; Mengech, A. S.; Rahman, K. M. M.; Tucker, L. C. N. Carbohydr. Res. 1982, 110, 207. (h) Fronza, G.; Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G. J. Carbohydr. Chem. 1983, 2, 225. (i) Hamada, Y.; Kawai, A.; Shioiri, T. Tetrahedron Lett. 1984, 25, 5413. (j) Hauser, F. M.; Ellenberger, S. R. J. Org. Chem. 1986, 51, 50. (k) Dyong, I.; Weigand, J.; Thiem, J. Liebigs Ann. Chem. 1986, 577. (l) Klemer, A.; Wilbers, H. Liebigs Ann. Chem. 1987, 815. (m) Hamada, Y.; Kawai, A.; Matsui, T.; Hara, O.; Shioiri, T. Tetrahedron 1990, 46, 4823. (n) Greven, R.; Jütten, P.; Scharf, H.-D. Carbohydr. Res. 1995, 275, 83. (o) Nicolaou, K. C.; Mitchell, H. J.; van Delft, F. L.; Rübsam, F.; Rodriguez, R. M. Angew. Chem., Int. Ed. 1998, 37, 1871. (p) Nicolaou, K. C.; Mitchell, J. J.; Jain, N. F.; Bando, T.; Hughes, R.; Winssinger, N.; Natarajan, S.; Koumbis, A. E. Chem. Eur. J. 1999, 5, 2648. (q) Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Vega, J. A. Angew. Chem., Int. Ed. 2000, 39, 2525. (r) Smith, G. R.; Giuliano, R. M. Carbohydr. Res. 2000, 323, 208. (s) Cutchins, W. W.; McDonald, F. E. Org. Lett. 2002, 4, 749.
31. Synthesis of vancosamine or its derivatives: (a) Thang, T. T.; Winternitz, F.; Olesker, A.; Lagrange, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1979, 153. (b) Dyong, I.; Friege, H. Chem. Ber. 1979, 112, 3273. (c) Thang, T. T.; Winternitz, F.; Olesker, A.; Lagrange, A.; Lukacs, G. Tetrahedron Lett. 1980, 21, 4495. (d) Ahmad, H. I.; Brimacombe, J. S.; Mengech, A. S.; Tucker, L. C. N. Carbohydr. Res. 1981, 93, 288. (e) Dyong, I.; Friege, H.; Luftmann, H.; Merten, H. Chem. Ber. 1981, 114, 2669. (f) Fronza, G.; Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G. Tetrahedron Lett. 1981, 22, 5073. (g) Brimacombe, J. S.; Mengech, A. S.; Rahman, K. M. M.; Tucker, L. C. N. Carbohydr. Res. 1982, 110, 207. (h) Fronza, G.; Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G. J. Carbohydr. Chem. 1983, 2, 225. (i) Hamada, Y.; Kawai, A.; Shioiri, T. Tetrahedron Lett. 1984, 25, 5413. (j) Hauser, F. M.; Ellenberger, S. R. J. Org. Chem. 1986, 51, 50. (k) Dyong, I.; Weigand, J.; Thiem, J. Liebigs Ann. Chem. 1986, 577. (l) Klemer, A.; Wilbers, H. Liebigs Ann. Chem. 1987, 815. (m) Hamada, Y.; Kawai, A.; Matsui, T.; Hara, O.; Shioiri, T. Tetrahedron 1990, 46, 4823. (n) Greven, R.; Jütten, P.; Scharf, H.-D. Carbohydr. Res. 1995, 275, 83. (o) Nicolaou, K. C.; Mitchell, H. J.; van Delft, F. L.; Rübsam, F.; Rodriguez, R. M. Angew. Chem., Int. Ed. 1998, 37, 1871. (p) Nicolaou, K. C.; Mitchell, J. J.; Jain, N. F.; Bando, T.; Hughes, R.; Winssinger, N.; Natarajan, S.; Koumbis, A. E. Chem. Eur. J. 1999, 5, 2648. (q) Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Vega, J. A. Angew. Chem., Int. Ed. 2000, 39, 2525. (r) Smith, G. R.; Giuliano, R. M. Carbohydr. Res. 2000, 323, 208. (s) Cutchins, W. W.; McDonald, F. E. Org. Lett. 2002, 4, 749.
32. Synthesis of vancosamine or its derivatives: (a) Thang, T. T.; Winternitz, F.; Olesker, A.; Lagrange, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1979, 153. (b) Dyong, I.; Friege, H. Chem. Ber. 1979, 112, 3273. (c) Thang, T. T.; Winternitz, F.; Olesker, A.; Lagrange, A.; Lukacs, G. Tetrahedron Lett. 1980, 21, 4495. (d) Ahmad, H. I.; Brimacombe, J. S.; Mengech, A. S.; Tucker, L. C. N. Carbohydr. Res. 1981, 93, 288. (e) Dyong, I.; Friege, H.; Luftmann, H.; Merten, H. Chem. Ber. 1981, 114, 2669. (f) Fronza, G.; Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G. Tetrahedron Lett. 1981, 22, 5073. (g) Brimacombe, J. S.; Mengech, A. S.; Rahman, K. M. M.; Tucker, L. C. N. Carbohydr. Res. 1982, 110, 207. (h) Fronza, G.; Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G. J. Carbohydr. Chem. 1983, 2, 225. (i) Hamada, Y.; Kawai, A.; Shioiri, T. Tetrahedron Lett. 1984, 25, 5413. (j) Hauser, F. M.; Ellenberger, S. R. J. Org. Chem. 1986, 51, 50. (k) Dyong, I.; Weigand, J.; Thiem, J. Liebigs Ann. Chem. 1986, 577. (l) Klemer, A.; Wilbers, H. Liebigs Ann. Chem. 1987, 815. (m) Hamada, Y.; Kawai, A.; Matsui, T.; Hara, O.; Shioiri, T. Tetrahedron 1990, 46, 4823. (n) Greven, R.; Jütten, P.; Scharf, H.-D. Carbohydr. Res. 1995, 275, 83. (o) Nicolaou, K. C.; Mitchell, H. J.; van Delft, F. L.; Rübsam, F.; Rodriguez, R. M. Angew. Chem., Int. Ed. 1998, 37, 1871. (p) Nicolaou, K. C.; Mitchell, J. J.; Jain, N. F.; Bando, T.; Hughes, R.; Winssinger, N.; Natarajan, S.; Koumbis, A. E. Chem. Eur. J. 1999, 5, 2648. (q) Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Vega, J. A. Angew. Chem., Int. Ed. 2000, 39, 2525. (r) Smith, G. R.; Giuliano, R. M. Carbohydr. Res. 2000, 323, 208. (s) Cutchins, W. W.; McDonald, F. E. Org. Lett. 2002, 4, 749.
33. Synthesis of vancosamine or its derivatives: (a) Thang, T. T.; Winternitz, F.; Olesker, A.; Lagrange, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1979, 153. (b) Dyong, I.; Friege, H. Chem. Ber. 1979, 112, 3273. (c) Thang, T. T.; Winternitz, F.; Olesker, A.; Lagrange, A.; Lukacs, G. Tetrahedron Lett. 1980, 21, 4495. (d) Ahmad, H. I.; Brimacombe, J. S.; Mengech, A. S.; Tucker, L. C. N. Carbohydr. Res. 1981, 93, 288. (e) Dyong, I.; Friege, H.; Luftmann, H.; Merten, H. Chem. Ber. 1981, 114, 2669. (f) Fronza, G.; Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G. Tetrahedron Lett. 1981, 22, 5073. (g) Brimacombe, J. S.; Mengech, A. S.; Rahman, K. M. M.; Tucker, L. C. N. Carbohydr. Res. 1982, 110, 207. (h) Fronza, G.; Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G. J. Carbohydr. Chem. 1983, 2, 225. (i) Hamada, Y.; Kawai, A.; Shioiri, T. Tetrahedron Lett. 1984, 25, 5413. (j) Hauser, F. M.; Ellenberger, S. R. J. Org. Chem. 1986, 51, 50. (k) Dyong, I.; Weigand, J.; Thiem, J. Liebigs Ann. Chem. 1986, 577. (l) Klemer, A.; Wilbers, H. Liebigs Ann. Chem. 1987, 815. (m) Hamada, Y.; Kawai, A.; Matsui, T.; Hara, O.; Shioiri, T. Tetrahedron 1990, 46, 4823. (n) Greven, R.; Jütten, P.; Scharf, H.-D. Carbohydr. Res. 1995, 275, 83. (o) Nicolaou, K. C.; Mitchell, H. J.; van Delft, F. L.; Rübsam, F.; Rodriguez, R. M. Angew. Chem., Int. Ed. 1998, 37, 1871. (p) Nicolaou, K. C.; Mitchell, J. J.; Jain, N. F.; Bando, T.; Hughes, R.; Winssinger, N.; Natarajan, S.; Koumbis, A. E. Chem. Eur. J. 1999, 5, 2648. (q) Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Vega, J. A. Angew. Chem., Int. Ed. 2000, 39, 2525. (r) Smith, G. R.; Giuliano, R. M. Carbohydr. Res. 2000, 323, 208. (s) Cutchins, W. W.; McDonald, F. E. Org. Lett. 2002, 4, 749.
34. Dushin, R. G.; Danishefsky, S. J. J. Am. Chem. Soc. 1992, 114, 3471.
35. McDonald, F. E.; Reddy, K. S.; Diaz, Y. J. Am. Chem. Soc. 2000, 122, 4304.
36. Espino, C. G.; Du Bois, J. Angew. Chem., Int. Ed. 2001, 40, 598.
37. (a) Marshall, J. A.; Wang, X. J. J. Org. Chem. 1991, 56, 3211.
38. (b) Marshall, J. A.; Wang, X. J. J. Org. Chem. 1992, 57, 1242.
39. For a review of this and related stereoselective addition reactions, see: Marshall, J. A. Chem. Rev. 1996, 96, 31.
40. Prepared from commercially available (R)-(+)-3-butyn-2-ol in two steps by the reported procedure: (a) Marshall, J. A.; Lu, Z.-H.; Johns, B. A. J. Org. Chem. 1998, 63, 817. (b) Marshall, J. A.; Grant, C. M. J. Org. Chem. 1999, 64, 8214.
41. Prepared from commercially available (R)-(+)-3-butyn-2-ol in two steps by the reported procedure: (a) Marshall, J. A.; Lu, Z.-H.; Johns, B. A. J. Org. Chem. 1998, 63, 817. (b) Marshall, J. A.; Grant, C. M. J. Org. Chem. 1999, 64, 8214.
42. 3, c 6.68): (a) Varelis, P.; Johnson, B. L. Aust. J. Chem. 1995, 48, 1775. (b) Solladié-Cavallo, A.; Bonne, F. Tetrahedron: Asymmetry 1996, 7, 171.
43. 3, c 6.68): (a) Varelis, P.; Johnson, B. L. Aust. J. Chem. 1995, 48, 1775. (b) Solladié-Cavallo, A.; Bonne, F. Tetrahedron: Asymmetry 1996, 7, 171.
44. Scheidt, K. A.; Bannister, T. D.; Tasaka, A.; Wendt, M. D.; Savall, B. M.; Fegley, G. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 6981.
45. 1H NMR spectrum: Marshall, J. A.; Chobanian, H. R. J. Org. Chem. 2000, 65, 8357. The reported enantiomeric excess of commercially available (R)-(+)-3-butyn-2-ol (Aldrich Chemical Company) was greater than 95%; therefore, a small amount of the (M)-isomer of the allenyl stannane was presumably involved in the reaction.
46. Kocovsky, P. Tetrahedron Lett. 1986, 27, 5521.
47. (a) Breslow, R.; Gellman, S. H. J. Am. Chem. Soc. 1983, 705, 6728.
48. (b) Nageli, I.; Baud, C.; Bernardinelli, G.; Jacquier, Y.; Moran, M.; Muller, P. Helv. Chim. Acta 1997, 80, 1087.
49. For a recent review on the approaches to synthesis of deoxy sugars, see: Kirschning, A.; Jesberger, M.; Schöning, K.-U. Synthesis 2001, 507.
50. For reviews of the syntheses of 3-amino-2,3,6-trideoxyhexoses, see: (a) Hauser, F. M.; Ellenberger, S. R. Chem. Rev. 1986, 86, 35. (b) Pelyás, I. F.; Monneret, C.; Herczegh, P. Synthetic Aspects of Aminodeoxy Sugars of Antibiotics; Springer-Verlag: Berlin, Germany, 1988.
51. For reviews of the syntheses of 3-amino-2,3,6-trideoxyhexoses, see: (a) Hauser, F. M.; Ellenberger, S. R. Chem. Rev. 1986, 86, 35. (b) Pelyás, I. F.; Monneret, C.; Herczegh, P. Synthetic Aspects of Aminodeoxy Sugars of Antibiotics; Springer-Verlag: Berlin, Germany, 1988.
52. For recent examples, see: (a) McDonald, F. E.; Wu, M. Org. Lett. 2002, 4, 3979. (b) Yadav, J. S.; Reddy, B. V. S.; Reddy, K. B.; Satyanarayana, M. Tetrahedron Lett. 2002, 43, 7009. (c) Pachamuthu, K.; Vankar, Y. D. J. Org. Chem. 2001, 66, 7511. (d) Toshima, K.; Nagai, H.; Ushiki, Y.; Matsumura, S. Synlett 1998, 1007.
53. For recent examples, see: (a) McDonald, F. E.; Wu, M. Org. Lett. 2002, 4, 3979. (b) Yadav, J. S.; Reddy, B. V. S.; Reddy, K. B.; Satyanarayana, M. Tetrahedron Lett. 2002, 43, 7009. (c) Pachamuthu, K.; Vankar, Y. D. J. Org. Chem. 2001, 66, 7511. (d) Toshima, K.; Nagai, H.; Ushiki, Y.; Matsumura, S. Synlett 1998, 1007.
54. For recent examples, see: (a) McDonald, F. E.; Wu, M. Org. Lett. 2002, 4, 3979. (b) Yadav, J. S.; Reddy, B. V. S.; Reddy, K. B.; Satyanarayana, M. Tetrahedron Lett. 2002, 43, 7009. (c) Pachamuthu, K.; Vankar, Y. D. J. Org. Chem. 2001, 66, 7511. (d) Toshima, K.; Nagai, H.; Ushiki, Y.; Matsumura, S. Synlett 1998, 1007.
55. For recent examples, see: (a) McDonald, F. E.; Wu, M. Org. Lett. 2002, 4, 3979. (b) Yadav, J. S.; Reddy, B. V. S.; Reddy, K. B.; Satyanarayana, M. Tetrahedron Lett. 2002, 43, 7009. (c) Pachamuthu, K.; Vankar, Y. D. J. Org. Chem. 2001, 66, 7511. (d) Toshima, K.; Nagai, H.; Ushiki, Y.; Matsumura, S. Synlett 1998, 1007.
56. For example, see: (a) Prandi, J.; Beau, J.-M. Tetrahedron Lett. 1989, 30, 4517. (b) Brown, D. S.; Bruno, M.; Davenport, R. J.; Ley, S. V. Tetrahedron 1989, 45, 4293. (c) Lesimple, P.; Beau, J.-M.; Sinay, P. Carbohydr. Res. 1987, 171, 289.
57. For example, see: (a) Prandi, J.; Beau, J.-M. Tetrahedron Lett. 1989, 30, 4517. (b) Brown, D. S.; Bruno, M.; Davenport, R. J.; Ley, S. V. Tetrahedron 1989, 45, 4293. (c) Lesimple, P.; Beau, J.-M.; Sinay, P. Carbohydr. Res. 1987, 171, 289.
58. For example, see: (a) Prandi, J.; Beau, J.-M. Tetrahedron Lett. 1989, 30, 4517. (b) Brown, D. S.; Bruno, M.; Davenport, R. J.; Ley, S. V. Tetrahedron 1989, 45, 4293. (c) Lesimple, P.; Beau, J.-M.; Sinay, P. Carbohydr. Res. 1987, 171, 289.