1,3-Dipolar cycloaddition reaction of D-glucose-derived nitrone with allyl alcohol: Synthesis of 2-hydroxy-1-deoxycastanospermine analogues

Journal of Organic Chemistry

Volumn 70, Issue 4, 2005, Pages 1356-1363

  Karanjule, Narayan S ^a   Markad, Shankar D ^a   Sharma, Tarun ^a   Sabharwal, Sushma G ^a   Puranik, Vedavati G ^b   Dhavale, Dilip D ^a  

^a UNIVERSITY OF PUNE   (India)

^b NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; AMINES; HYDROGENATION; REMOVAL; SUBSTITUTION REACTIONS; SUGAR (SUCROSE); SYNTHESIS (CHEMICAL);

ALKALOIDS; HYDROGENOLYSIS; REGIOSELECTIVITY; TOSYLATION;

GLUCOSE;

2 HYDROXY 1 DEOXY 8A EPICASTANOSPERMINE; 2 HYDROXY 1 DEOXYCASTANOSPERMINE; ALLYL ALCOHOL; ALPHA GALACTOSIDASE; ALPHA GLUCOSIDASE; ALPHA MANNOSIDASE; BETA GALACTOSIDASE; BETA GLUCOSIDASE; CASTANOSPERMINE DERIVATIVE; GLUCOSE; INDOLIZIDINE ALKALOID; ISOXAZOLIDINE DERIVATIVE; NITRONE; NOJIRIMYCIN; UNCLASSIFIED DRUG;

ACQUIRED IMMUNE DEFICIENCY SYNDROME; ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; ARTICLE; CYCLOADDITION; DIABETES MELLITUS; DRUG SYNTHESIS; HYDROGENATION; HYDROGENOLYSIS; IC 50; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; X RAY ANALYSIS;

GLUCOSE; GLYCOSIDE HYDROLASES; INDOLIZINES; INHIBITORY CONCENTRATION 50; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NITROGEN OXIDES; PROPANOLS; STEREOISOMERISM;

EID: 13844314454     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048176x     Document Type: Article

References (64)

1. For reviews on the 1,3-dipolar cycloaddition of nitrones, see: (a) Osborn, H. M.; Gemmell, N.; Harwood, L. M. J. Chem Soc., Perkin Trans. 1 2002, 2419-2438. (b) Frederickson, M. Teterahedron 1997, 53, 403-425. (c) Confalone, P. N.; Huie, E. M. Org. React. 1988, 36, 1-173. (d) Torseel, K. B. G. Nitrite Oxides, Nitrones and Nitronates in Organic synthesis; Feuer H., Ed.; VCH: Weinheim, Germany, 1988. (e) Ferrier, R. J.; Middleton, S. Chem. Rev. 1993, 93, 2779-2831. (f) Gothelf, K. V.; Jorgensen, K. A. Chem. Rev. 1998, 98, 8, 863-910. (g) Adams, J. P.; Box, D. S. J. Chem. Soc., Perkin Trans. 1 1999, 749-764. (h) Karlsson, S.; Hogberg, H. E. Org. Prep. Proced. Int. 2001, 33, 103-172. (i) Koumbis, A. E.; Gallos, J. K. Curr. Org. Chem. 2003, 7, 585-628. (j) Padwa, A.; Pearson, W. H. J. Nat. Prod. 2004, 67, 1074-1074. (k) Padwa, A.; Pearson, W. H. Org. Process Res. Dev. 2004, 8, 293-293. (1) Padwa, A.; Pearson, W. H. J. Am. Chem. Soc. 2002, 124, 12633-12634. (m) Cycloadditon Reactions in Organic synthesis; Carruthers, W., Ed.; Tetrahedron organic chemistry series; Pergamon Press: New York, 1990; Vol. 8, pp 269-314. (n) Advances in Cycloaddition; Curran, D. P., Ed.; JAI Press: London, UK, 1988, Vol. 1; 1990, Vol. 2; 1993, Vol. 3. (o) Gothelf, K. V. In Cycloaddition reactions in organic synthesis; Kobayashi, S., Jorgensen, K. A., Eds.; Wiley-VCH;, Weinheim, Germany, 2002; Chapter 6, pp 211-247. (p) Kanemasa, S. In Cycloaddition reactions in Organic synthesis; Kobayashi, S., Jorgensen, K. A., Eds.; Wiley-VCH: Weinheim, Germany, 2002; Chapter 7, pp 249-300.
2. For reviews on the 1,3-dipolar cycloaddition of nitrones, see: (a) Osborn, H. M.; Gemmell, N.; Harwood, L. M. J. Chem Soc., Perkin Trans. 1 2002, 2419-2438. (b) Frederickson, M. Teterahedron 1997, 53, 403-425. (c) Confalone, P. N.; Huie, E. M. Org. React. 1988, 36, 1-173. (d) Torseel, K. B. G. Nitrite Oxides, Nitrones and Nitronates in Organic synthesis; Feuer H., Ed.; VCH: Weinheim, Germany, 1988. (e) Ferrier, R. J.; Middleton, S. Chem. Rev. 1993, 93, 2779-2831. (f) Gothelf, K. V.; Jorgensen, K. A. Chem. Rev. 1998, 98, 8, 863-910. (g) Adams, J. P.; Box, D. S. J. Chem. Soc., Perkin Trans. 1 1999, 749-764. (h) Karlsson, S.; Hogberg, H. E. Org. Prep. Proced. Int. 2001, 33, 103-172. (i) Koumbis, A. E.; Gallos, J. K. Curr. Org. Chem. 2003, 7, 585-628. (j) Padwa, A.; Pearson, W. H. J. Nat. Prod. 2004, 67, 1074-1074. (k) Padwa, A.; Pearson, W. H. Org. Process Res. Dev. 2004, 8, 293-293. (1) Padwa, A.; Pearson, W. H. J. Am. Chem. Soc. 2002, 124, 12633-12634. (m) Cycloadditon Reactions in Organic synthesis; Carruthers, W., Ed.; Tetrahedron organic chemistry series; Pergamon Press: New York, 1990; Vol. 8, pp 269-314. (n) Advances in Cycloaddition; Curran, D. P., Ed.; JAI Press: London, UK, 1988, Vol. 1; 1990, Vol. 2; 1993, Vol. 3. (o) Gothelf, K. V. In Cycloaddition reactions in organic synthesis; Kobayashi, S., Jorgensen, K. A., Eds.; Wiley-VCH;, Weinheim, Germany, 2002; Chapter 6, pp 211-247. (p) Kanemasa, S. In Cycloaddition reactions in Organic synthesis; Kobayashi, S., Jorgensen, K. A., Eds.; Wiley-VCH: Weinheim, Germany, 2002; Chapter 7, pp 249-300.
3. For reviews on the 1,3-dipolar cycloaddition of nitrones, see: (a) Osborn, H. M.; Gemmell, N.; Harwood, L. M. J. Chem Soc., Perkin Trans. 1 2002, 2419-2438. (b) Frederickson, M. Teterahedron 1997, 53, 403-425. (c) Confalone, P. N.; Huie, E. M. Org. React. 1988, 36, 1-173. (d) Torseel, K. B. G. Nitrite Oxides, Nitrones and Nitronates in Organic synthesis; Feuer H., Ed.; VCH: Weinheim, Germany, 1988. (e) Ferrier, R. J.; Middleton, S. Chem. Rev. 1993, 93, 2779-2831. (f) Gothelf, K. V.; Jorgensen, K. A. Chem. Rev. 1998, 98, 8, 863-910. (g) Adams, J. P.; Box, D. S. J. Chem. Soc., Perkin Trans. 1 1999, 749-764. (h) Karlsson, S.; Hogberg, H. E. Org. Prep. Proced. Int. 2001, 33, 103-172. (i) Koumbis, A. E.; Gallos, J. K. Curr. Org. Chem. 2003, 7, 585-628. (j) Padwa, A.; Pearson, W. H. J. Nat. Prod. 2004, 67, 1074-1074. (k) Padwa, A.; Pearson, W. H. Org. Process Res. Dev. 2004, 8, 293-293. (1) Padwa, A.; Pearson, W. H. J. Am. Chem. Soc. 2002, 124, 12633-12634. (m) Cycloadditon Reactions in Organic synthesis; Carruthers, W., Ed.; Tetrahedron organic chemistry series; Pergamon Press: New York, 1990; Vol. 8, pp 269-314. (n) Advances in Cycloaddition; Curran, D. P., Ed.; JAI Press: London, UK, 1988, Vol. 1; 1990, Vol. 2; 1993, Vol. 3. (o) Gothelf, K. V. In Cycloaddition reactions in organic synthesis; Kobayashi, S., Jorgensen, K. A., Eds.; Wiley-VCH;, Weinheim, Germany, 2002; Chapter 6, pp 211-247. (p) Kanemasa, S. In Cycloaddition reactions in Organic synthesis; Kobayashi, S., Jorgensen, K. A., Eds.; Wiley-VCH: Weinheim, Germany, 2002; Chapter 7, pp 249-300.
4. For reviews on the 1,3-dipolar cycloaddition of nitrones, see: (a) Osborn, H. M.; Gemmell, N.; Harwood, L. M. J. Chem Soc., Perkin Trans. 1 2002, 2419-2438. (b) Frederickson, M. Teterahedron 1997, 53, 403-425. (c) Confalone, P. N.; Huie, E. M. Org. React. 1988, 36, 1-173. (d) Torseel, K. B. G. Nitrite Oxides, Nitrones and Nitronates in Organic synthesis; Feuer H., Ed.; VCH: Weinheim, Germany, 1988. (e) Ferrier, R. J.; Middleton, S. Chem. Rev. 1993, 93, 2779-2831. (f) Gothelf, K. V.; Jorgensen, K. A. Chem. Rev. 1998, 98, 8, 863-910. (g) Adams, J. P.; Box, D. S. J. Chem. Soc., Perkin Trans. 1 1999, 749-764. (h) Karlsson, S.; Hogberg, H. E. Org. Prep. Proced. Int. 2001, 33, 103-172. (i) Koumbis, A. E.; Gallos, J. K. Curr. Org. Chem. 2003, 7, 585-628. (j) Padwa, A.; Pearson, W. H. J. Nat. Prod. 2004, 67, 1074-1074. (k) Padwa, A.; Pearson, W. H. Org. Process Res. Dev. 2004, 8, 293-293. (1) Padwa, A.; Pearson, W. H. J. Am. Chem. Soc. 2002, 124, 12633-12634. (m) Cycloadditon Reactions in Organic synthesis; Carruthers, W., Ed.; Tetrahedron organic chemistry series; Pergamon Press: New York, 1990; Vol. 8, pp 269-314. (n) Advances in Cycloaddition; Curran, D. P., Ed.; JAI Press: London, UK, 1988, Vol. 1; 1990, Vol. 2; 1993, Vol. 3. (o) Gothelf, K. V. In Cycloaddition reactions in organic synthesis; Kobayashi, S., Jorgensen, K. A., Eds.; Wiley-VCH;, Weinheim, Germany, 2002; Chapter 6, pp 211-247. (p) Kanemasa, S. In Cycloaddition reactions in Organic synthesis; Kobayashi, S., Jorgensen, K. A., Eds.; Wiley-VCH: Weinheim, Germany, 2002; Chapter 7, pp 249-300.
5. For reviews on the 1,3-dipolar cycloaddition of nitrones, see: (a) Osborn, H. M.; Gemmell, N.; Harwood, L. M. J. Chem Soc., Perkin Trans. 1 2002, 2419-2438. (b) Frederickson, M. Teterahedron 1997, 53, 403-425. (c) Confalone, P. N.; Huie, E. M. Org. React. 1988, 36, 1-173. (d) Torseel, K. B. G. Nitrite Oxides, Nitrones and Nitronates in Organic synthesis; Feuer H., Ed.; VCH: Weinheim, Germany, 1988. (e) Ferrier, R. J.; Middleton, S. Chem. Rev. 1993, 93, 2779-2831. (f) Gothelf, K. V.; Jorgensen, K. A. Chem. Rev. 1998, 98, 8, 863-910. (g) Adams, J. P.; Box, D. S. J. Chem. Soc., Perkin Trans. 1 1999, 749-764. (h) Karlsson, S.; Hogberg, H. E. Org. Prep. Proced. Int. 2001, 33, 103-172. (i) Koumbis, A. E.; Gallos, J. K. Curr. Org. Chem. 2003, 7, 585-628. (j) Padwa, A.; Pearson, W. H. J. Nat. Prod. 2004, 67, 1074-1074. (k) Padwa, A.; Pearson, W. H. Org. Process Res. Dev. 2004, 8, 293-293. (1) Padwa, A.; Pearson, W. H. J. Am. Chem. Soc. 2002, 124, 12633-12634. (m) Cycloadditon Reactions in Organic synthesis; Carruthers, W., Ed.; Tetrahedron organic chemistry series; Pergamon Press: New York, 1990; Vol. 8, pp 269-314. (n) Advances in Cycloaddition; Curran, D. P., Ed.; JAI Press: London, UK, 1988, Vol. 1; 1990, Vol. 2; 1993, Vol. 3. (o) Gothelf, K. V. In Cycloaddition reactions in organic synthesis; Kobayashi, S., Jorgensen, K. A., Eds.; Wiley-VCH;, Weinheim, Germany, 2002; Chapter 6, pp 211-247. (p) Kanemasa, S. In Cycloaddition reactions in Organic synthesis; Kobayashi, S., Jorgensen, K. A., Eds.; Wiley-VCH: Weinheim, Germany, 2002; Chapter 7, pp 249-300.
6. For reviews on the 1,3-dipolar cycloaddition of nitrones, see: (a) Osborn, H. M.; Gemmell, N.; Harwood, L. M. J. Chem Soc., Perkin Trans. 1 2002, 2419-2438. (b) Frederickson, M. Teterahedron 1997, 53, 403-425. (c) Confalone, P. N.; Huie, E. M. Org. React. 1988, 36, 1-173. (d) Torseel, K. B. G. Nitrite Oxides, Nitrones and Nitronates in Organic synthesis; Feuer H., Ed.; VCH: Weinheim, Germany, 1988. (e) Ferrier, R. J.; Middleton, S. Chem. Rev. 1993, 93, 2779-2831. (f) Gothelf, K. V.; Jorgensen, K. A. Chem. Rev. 1998, 98, 8, 863-910. (g) Adams, J. P.; Box, D. S. J. Chem. Soc., Perkin Trans. 1 1999, 749-764. (h) Karlsson, S.; Hogberg, H. E. Org. Prep. Proced. Int. 2001, 33, 103-172. (i) Koumbis, A. E.; Gallos, J. K. Curr. Org. Chem. 2003, 7, 585-628. (j) Padwa, A.; Pearson, W. H. J. Nat. Prod. 2004, 67, 1074-1074. (k) Padwa, A.; Pearson, W. H. Org. Process Res. Dev. 2004, 8, 293-293. (1) Padwa, A.; Pearson, W. H. J. Am. Chem. Soc. 2002, 124, 12633-12634. (m) Cycloadditon Reactions in Organic synthesis; Carruthers, W., Ed.; Tetrahedron organic chemistry series; Pergamon Press: New York, 1990; Vol. 8, pp 269-314. (n) Advances in Cycloaddition; Curran, D. P., Ed.; JAI Press: London, UK, 1988, Vol. 1; 1990, Vol. 2; 1993, Vol. 3. (o) Gothelf, K. V. In Cycloaddition reactions in organic synthesis; Kobayashi, S., Jorgensen, K. A., Eds.; Wiley-VCH;, Weinheim, Germany, 2002; Chapter 6, pp 211-247. (p) Kanemasa, S. In Cycloaddition reactions in Organic synthesis; Kobayashi, S., Jorgensen, K. A., Eds.; Wiley-VCH: Weinheim, Germany, 2002; Chapter 7, pp 249-300.
7. For reviews on the 1,3-dipolar cycloaddition of nitrones, see: (a) Osborn, H. M.; Gemmell, N.; Harwood, L. M. J. Chem Soc., Perkin Trans. 1 2002, 2419-2438. (b) Frederickson, M. Teterahedron 1997, 53, 403-425. (c) Confalone, P. N.; Huie, E. M. Org. React. 1988, 36, 1-173. (d) Torseel, K. B. G. Nitrite Oxides, Nitrones and Nitronates in Organic synthesis; Feuer H., Ed.; VCH: Weinheim, Germany, 1988. (e) Ferrier, R. J.; Middleton, S. Chem. Rev. 1993, 93, 2779-2831. (f) Gothelf, K. V.; Jorgensen, K. A. Chem. Rev. 1998, 98, 8, 863-910. (g) Adams, J. P.; Box, D. S. J. Chem. Soc., Perkin Trans. 1 1999, 749-764. (h) Karlsson, S.; Hogberg, H. E. Org. Prep. Proced. Int. 2001, 33, 103-172. (i) Koumbis, A. E.; Gallos, J. K. Curr. Org. Chem. 2003, 7, 585-628. (j) Padwa, A.; Pearson, W. H. J. Nat. Prod. 2004, 67, 1074-1074. (k) Padwa, A.; Pearson, W. H. Org. Process Res. Dev. 2004, 8, 293-293. (1) Padwa, A.; Pearson, W. H. J. Am. Chem. Soc. 2002, 124, 12633-12634. (m) Cycloadditon Reactions in Organic synthesis; Carruthers, W., Ed.; Tetrahedron organic chemistry series; Pergamon Press: New York, 1990; Vol. 8, pp 269-314. (n) Advances in Cycloaddition; Curran, D. P., Ed.; JAI Press: London, UK, 1988, Vol. 1; 1990, Vol. 2; 1993, Vol. 3. (o) Gothelf, K. V. In Cycloaddition reactions in organic synthesis; Kobayashi, S., Jorgensen, K. A., Eds.; Wiley-VCH;, Weinheim, Germany, 2002; Chapter 6, pp 211-247. (p) Kanemasa, S. In Cycloaddition reactions in Organic synthesis; Kobayashi, S., Jorgensen, K. A., Eds.; Wiley-VCH: Weinheim, Germany, 2002; Chapter 7, pp 249-300.
8. For reviews on the 1,3-dipolar cycloaddition of nitrones, see: (a) Osborn, H. M.; Gemmell, N.; Harwood, L. M. J. Chem Soc., Perkin Trans. 1 2002, 2419-2438. (b) Frederickson, M. Teterahedron 1997, 53, 403-425. (c) Confalone, P. N.; Huie, E. M. Org. React. 1988, 36, 1-173. (d) Torseel, K. B. G. Nitrite Oxides, Nitrones and Nitronates in Organic synthesis; Feuer H., Ed.; VCH: Weinheim, Germany, 1988. (e) Ferrier, R. J.; Middleton, S. Chem. Rev. 1993, 93, 2779-2831. (f) Gothelf, K. V.; Jorgensen, K. A. Chem. Rev. 1998, 98, 8, 863-910. (g) Adams, J. P.; Box, D. S. J. Chem. Soc., Perkin Trans. 1 1999, 749-764. (h) Karlsson, S.; Hogberg, H. E. Org. Prep. Proced. Int. 2001, 33, 103-172. (i) Koumbis, A. E.; Gallos, J. K. Curr. Org. Chem. 2003, 7, 585-628. (j) Padwa, A.; Pearson, W. H. J. Nat. Prod. 2004, 67, 1074-1074. (k) Padwa, A.; Pearson, W. H. Org. Process Res. Dev. 2004, 8, 293-293. (1) Padwa, A.; Pearson, W. H. J. Am. Chem. Soc. 2002, 124, 12633-12634. (m) Cycloadditon Reactions in Organic synthesis; Carruthers, W., Ed.; Tetrahedron organic chemistry series; Pergamon Press: New York, 1990; Vol. 8, pp 269-314. (n) Advances in Cycloaddition; Curran, D. P., Ed.; JAI Press: London, UK, 1988, Vol. 1; 1990, Vol. 2; 1993, Vol. 3. (o) Gothelf, K. V. In Cycloaddition reactions in organic synthesis; Kobayashi, S., Jorgensen, K. A., Eds.; Wiley-VCH;, Weinheim, Germany, 2002; Chapter 6, pp 211-247. (p) Kanemasa, S. In Cycloaddition reactions in Organic synthesis; Kobayashi, S., Jorgensen, K. A., Eds.; Wiley-VCH: Weinheim, Germany, 2002; Chapter 7, pp 249-300.
9. For reviews on the 1,3-dipolar cycloaddition of nitrones, see: (a) Osborn, H. M.; Gemmell, N.; Harwood, L. M. J. Chem Soc., Perkin Trans. 1 2002, 2419-2438. (b) Frederickson, M. Teterahedron 1997, 53, 403-425. (c) Confalone, P. N.; Huie, E. M. Org. React. 1988, 36, 1-173. (d) Torseel, K. B. G. Nitrite Oxides, Nitrones and Nitronates in Organic synthesis; Feuer H., Ed.; VCH: Weinheim, Germany, 1988. (e) Ferrier, R. J.; Middleton, S. Chem. Rev. 1993, 93, 2779-2831. (f) Gothelf, K. V.; Jorgensen, K. A. Chem. Rev. 1998, 98, 8, 863-910. (g) Adams, J. P.; Box, D. S. J. Chem. Soc., Perkin Trans. 1 1999, 749-764. (h) Karlsson, S.; Hogberg, H. E. Org. Prep. Proced. Int. 2001, 33, 103-172. (i) Koumbis, A. E.; Gallos, J. K. Curr. Org. Chem. 2003, 7, 585-628. (j) Padwa, A.; Pearson, W. H. J. Nat. Prod. 2004, 67, 1074-1074. (k) Padwa, A.; Pearson, W. H. Org. Process Res. Dev. 2004, 8, 293-293. (1) Padwa, A.; Pearson, W. H. J. Am. Chem. Soc. 2002, 124, 12633-12634. (m) Cycloadditon Reactions in Organic synthesis; Carruthers, W., Ed.; Tetrahedron organic chemistry series; Pergamon Press: New York, 1990; Vol. 8, pp 269-314. (n) Advances in Cycloaddition; Curran, D. P., Ed.; JAI Press: London, UK, 1988, Vol. 1; 1990, Vol. 2; 1993, Vol. 3. (o) Gothelf, K. V. In Cycloaddition reactions in organic synthesis; Kobayashi, S., Jorgensen, K. A., Eds.; Wiley-VCH;, Weinheim, Germany, 2002; Chapter 6, pp 211-247. (p) Kanemasa, S. In Cycloaddition reactions in Organic synthesis; Kobayashi, S., Jorgensen, K. A., Eds.; Wiley-VCH: Weinheim, Germany, 2002; Chapter 7, pp 249-300.
10. For reviews on the 1,3-dipolar cycloaddition of nitrones, see: (a) Osborn, H. M.; Gemmell, N.; Harwood, L. M. J. Chem Soc., Perkin Trans. 1 2002, 2419-2438. (b) Frederickson, M. Teterahedron 1997, 53, 403-425. (c) Confalone, P. N.; Huie, E. M. Org. React. 1988, 36, 1-173. (d) Torseel, K. B. G. Nitrite Oxides, Nitrones and Nitronates in Organic synthesis; Feuer H., Ed.; VCH: Weinheim, Germany, 1988. (e) Ferrier, R. J.; Middleton, S. Chem. Rev. 1993, 93, 2779-2831. (f) Gothelf, K. V.; Jorgensen, K. A. Chem. Rev. 1998, 98, 8, 863-910. (g) Adams, J. P.; Box, D. S. J. Chem. Soc., Perkin Trans. 1 1999, 749-764. (h) Karlsson, S.; Hogberg, H. E. Org. Prep. Proced. Int. 2001, 33, 103-172. (i) Koumbis, A. E.; Gallos, J. K. Curr. Org. Chem. 2003, 7, 585-628. (j) Padwa, A.; Pearson, W. H. J. Nat. Prod. 2004, 67, 1074-1074. (k) Padwa, A.; Pearson, W. H. Org. Process Res. Dev. 2004, 8, 293-293. (1) Padwa, A.; Pearson, W. H. J. Am. Chem. Soc. 2002, 124, 12633-12634. (m) Cycloadditon Reactions in Organic synthesis; Carruthers, W., Ed.; Tetrahedron organic chemistry series; Pergamon Press: New York, 1990; Vol. 8, pp 269-314. (n) Advances in Cycloaddition; Curran, D. P., Ed.; JAI Press: London, UK, 1988, Vol. 1; 1990, Vol. 2; 1993, Vol. 3. (o) Gothelf, K. V. In Cycloaddition reactions in organic synthesis; Kobayashi, S., Jorgensen, K. A., Eds.; Wiley-VCH;, Weinheim, Germany, 2002; Chapter 6, pp 211-247. (p) Kanemasa, S. In Cycloaddition reactions in Organic synthesis; Kobayashi, S., Jorgensen, K. A., Eds.; Wiley-VCH: Weinheim, Germany, 2002; Chapter 7, pp 249-300.
11. For reviews on the 1,3-dipolar cycloaddition of nitrones, see: (a) Osborn, H. M.; Gemmell, N.; Harwood, L. M. J. Chem Soc., Perkin Trans. 1 2002, 2419-2438. (b) Frederickson, M. Teterahedron 1997, 53, 403-425. (c) Confalone, P. N.; Huie, E. M. Org. React. 1988, 36, 1-173. (d) Torseel, K. B. G. Nitrite Oxides, Nitrones and Nitronates in Organic synthesis; Feuer H., Ed.; VCH: Weinheim, Germany, 1988. (e) Ferrier, R. J.; Middleton, S. Chem. Rev. 1993, 93, 2779-2831. (f) Gothelf, K. V.; Jorgensen, K. A. Chem. Rev. 1998, 98, 8, 863-910. (g) Adams, J. P.; Box, D. S. J. Chem. Soc., Perkin Trans. 1 1999, 749-764. (h) Karlsson, S.; Hogberg, H. E. Org. Prep. Proced. Int. 2001, 33, 103-172. (i) Koumbis, A. E.; Gallos, J. K. Curr. Org. Chem. 2003, 7, 585-628. (j) Padwa, A.; Pearson, W. H. J. Nat. Prod. 2004, 67, 1074-1074. (k) Padwa, A.; Pearson, W. H. Org. Process Res. Dev. 2004, 8, 293-293. (1) Padwa, A.; Pearson, W. H. J. Am. Chem. Soc. 2002, 124, 12633-12634. (m) Cycloadditon Reactions in Organic synthesis; Carruthers, W., Ed.; Tetrahedron organic chemistry series; Pergamon Press: New York, 1990; Vol. 8, pp 269-314. (n) Advances in Cycloaddition; Curran, D. P., Ed.; JAI Press: London, UK, 1988, Vol. 1; 1990, Vol. 2; 1993, Vol. 3. (o) Gothelf, K. V. In Cycloaddition reactions in organic synthesis; Kobayashi, S., Jorgensen, K. A., Eds.; Wiley-VCH;, Weinheim, Germany, 2002; Chapter 6, pp 211-247. (p) Kanemasa, S. In Cycloaddition reactions in Organic synthesis; Kobayashi, S., Jorgensen, K. A., Eds.; Wiley-VCH: Weinheim, Germany, 2002; Chapter 7, pp 249-300.
12. For reviews on the 1,3-dipolar cycloaddition of nitrones, see: (a) Osborn, H. M.; Gemmell, N.; Harwood, L. M. J. Chem Soc., Perkin Trans. 1 2002, 2419-2438. (b) Frederickson, M. Teterahedron 1997, 53, 403-425. (c) Confalone, P. N.; Huie, E. M. Org. React. 1988, 36, 1-173. (d) Torseel, K. B. G. Nitrite Oxides, Nitrones and Nitronates in Organic synthesis; Feuer H., Ed.; VCH: Weinheim, Germany, 1988. (e) Ferrier, R. J.; Middleton, S. Chem. Rev. 1993, 93, 2779-2831. (f) Gothelf, K. V.; Jorgensen, K. A. Chem. Rev. 1998, 98, 8, 863-910. (g) Adams, J. P.; Box, D. S. J. Chem. Soc., Perkin Trans. 1 1999, 749-764. (h) Karlsson, S.; Hogberg, H. E. Org. Prep. Proced. Int. 2001, 33, 103-172. (i) Koumbis, A. E.; Gallos, J. K. Curr. Org. Chem. 2003, 7, 585-628. (j) Padwa, A.; Pearson, W. H. J. Nat. Prod. 2004, 67, 1074-1074. (k) Padwa, A.; Pearson, W. H. Org. Process Res. Dev. 2004, 8, 293-293. (1) Padwa, A.; Pearson, W. H. J. Am. Chem. Soc. 2002, 124, 12633-12634. (m) Cycloadditon Reactions in Organic synthesis; Carruthers, W., Ed.; Tetrahedron organic chemistry series; Pergamon Press: New York, 1990; Vol. 8, pp 269-314. (n) Advances in Cycloaddition; Curran, D. P., Ed.; JAI Press: London, UK, 1988, Vol. 1; 1990, Vol. 2; 1993, Vol. 3. (o) Gothelf, K. V. In Cycloaddition reactions in organic synthesis; Kobayashi, S., Jorgensen, K. A., Eds.; Wiley-VCH;, Weinheim, Germany, 2002; Chapter 6, pp 211-247. (p) Kanemasa, S. In Cycloaddition reactions in Organic synthesis; Kobayashi, S., Jorgensen, K. A., Eds.; Wiley-VCH: Weinheim, Germany, 2002; Chapter 7, pp 249-300.
13. For reviews on the 1,3-dipolar cycloaddition of nitrones, see: (a) Osborn, H. M.; Gemmell, N.; Harwood, L. M. J. Chem Soc., Perkin Trans. 1 2002, 2419-2438. (b) Frederickson, M. Teterahedron 1997, 53, 403-425. (c) Confalone, P. N.; Huie, E. M. Org. React. 1988, 36, 1-173. (d) Torseel, K. B. G. Nitrite Oxides, Nitrones and Nitronates in Organic synthesis; Feuer H., Ed.; VCH: Weinheim, Germany, 1988. (e) Ferrier, R. J.; Middleton, S. Chem. Rev. 1993, 93, 2779-2831. (f) Gothelf, K. V.; Jorgensen, K. A. Chem. Rev. 1998, 98, 8, 863-910. (g) Adams, J. P.; Box, D. S. J. Chem. Soc., Perkin Trans. 1 1999, 749-764. (h) Karlsson, S.; Hogberg, H. E. Org. Prep. Proced. Int. 2001, 33, 103-172. (i) Koumbis, A. E.; Gallos, J. K. Curr. Org. Chem. 2003, 7, 585-628. (j) Padwa, A.; Pearson, W. H. J. Nat. Prod. 2004, 67, 1074-1074. (k) Padwa, A.; Pearson, W. H. Org. Process Res. Dev. 2004, 8, 293-293. (1) Padwa, A.; Pearson, W. H. J. Am. Chem. Soc. 2002, 124, 12633-12634. (m) Cycloadditon Reactions in Organic synthesis; Carruthers, W., Ed.; Tetrahedron organic chemistry series; Pergamon Press: New York, 1990; Vol. 8, pp 269-314. (n) Advances in Cycloaddition; Curran, D. P., Ed.; JAI Press: London, UK, 1988, Vol. 1; 1990, Vol. 2; 1993, Vol. 3. (o) Gothelf, K. V. In Cycloaddition reactions in organic synthesis; Kobayashi, S., Jorgensen, K. A., Eds.; Wiley-VCH;, Weinheim, Germany, 2002; Chapter 6, pp 211-247. (p) Kanemasa, S. In Cycloaddition reactions in Organic synthesis; Kobayashi, S., Jorgensen, K. A., Eds.; Wiley-VCH: Weinheim, Germany, 2002; Chapter 7, pp 249-300.
14. For reviews on the 1,3-dipolar cycloaddition of nitrones, see: (a) Osborn, H. M.; Gemmell, N.; Harwood, L. M. J. Chem Soc., Perkin Trans. 1 2002, 2419-2438. (b) Frederickson, M. Teterahedron 1997, 53, 403-425. (c) Confalone, P. N.; Huie, E. M. Org. React. 1988, 36, 1-173. (d) Torseel, K. B. G. Nitrite Oxides, Nitrones and Nitronates in Organic synthesis; Feuer H., Ed.; VCH: Weinheim, Germany, 1988. (e) Ferrier, R. J.; Middleton, S. Chem. Rev. 1993, 93, 2779-2831. (f) Gothelf, K. V.; Jorgensen, K. A. Chem. Rev. 1998, 98, 8, 863-910. (g) Adams, J. P.; Box, D. S. J. Chem. Soc., Perkin Trans. 1 1999, 749-764. (h) Karlsson, S.; Hogberg, H. E. Org. Prep. Proced. Int. 2001, 33, 103-172. (i) Koumbis, A. E.; Gallos, J. K. Curr. Org. Chem. 2003, 7, 585-628. (j) Padwa, A.; Pearson, W. H. J. Nat. Prod. 2004, 67, 1074-1074. (k) Padwa, A.; Pearson, W. H. Org. Process Res. Dev. 2004, 8, 293-293. (1) Padwa, A.; Pearson, W. H. J. Am. Chem. Soc. 2002, 124, 12633-12634. (m) Cycloadditon Reactions in Organic synthesis; Carruthers, W., Ed.; Tetrahedron organic chemistry series; Pergamon Press: New York, 1990; Vol. 8, pp 269-314. (n) Advances in Cycloaddition; Curran, D. P., Ed.; JAI Press: London, UK, 1988, Vol. 1; 1990, Vol. 2; 1993, Vol. 3. (o) Gothelf, K. V. In Cycloaddition reactions in organic synthesis; Kobayashi, S., Jorgensen, K. A., Eds.; Wiley-VCH;, Weinheim, Germany, 2002; Chapter 6, pp 211-247. (p) Kanemasa, S. In Cycloaddition reactions in Organic synthesis; Kobayashi, S., Jorgensen, K. A., Eds.; Wiley-VCH: Weinheim, Germany, 2002; Chapter 7, pp 249-300.
15. For reviews on the 1,3-dipolar cycloaddition of nitrones, see: (a) Osborn, H. M.; Gemmell, N.; Harwood, L. M. J. Chem Soc., Perkin Trans. 1 2002, 2419-2438. (b) Frederickson, M. Teterahedron 1997, 53, 403-425. (c) Confalone, P. N.; Huie, E. M. Org. React. 1988, 36, 1-173. (d) Torseel, K. B. G. Nitrite Oxides, Nitrones and Nitronates in Organic synthesis; Feuer H., Ed.; VCH: Weinheim, Germany, 1988. (e) Ferrier, R. J.; Middleton, S. Chem. Rev. 1993, 93, 2779-2831. (f) Gothelf, K. V.; Jorgensen, K. A. Chem. Rev. 1998, 98, 8, 863-910. (g) Adams, J. P.; Box, D. S. J. Chem. Soc., Perkin Trans. 1 1999, 749-764. (h) Karlsson, S.; Hogberg, H. E. Org. Prep. Proced. Int. 2001, 33, 103-172. (i) Koumbis, A. E.; Gallos, J. K. Curr. Org. Chem. 2003, 7, 585-628. (j) Padwa, A.; Pearson, W. H. J. Nat. Prod. 2004, 67, 1074-1074. (k) Padwa, A.; Pearson, W. H. Org. Process Res. Dev. 2004, 8, 293-293. (1) Padwa, A.; Pearson, W. H. J. Am. Chem. Soc. 2002, 124, 12633-12634. (m) Cycloadditon Reactions in Organic synthesis; Carruthers, W., Ed.; Tetrahedron organic chemistry series; Pergamon Press: New York, 1990; Vol. 8, pp 269-314. (n) Advances in Cycloaddition; Curran, D. P., Ed.; JAI Press: London, UK, 1988, Vol. 1; 1990, Vol. 2; 1993, Vol. 3. (o) Gothelf, K. V. In Cycloaddition reactions in organic synthesis; Kobayashi, S., Jorgensen, K. A., Eds.; Wiley-VCH;, Weinheim, Germany, 2002; Chapter 6, pp 211-247. (p) Kanemasa, S. In Cycloaddition reactions in Organic synthesis; Kobayashi, S., Jorgensen, K. A., Eds.; Wiley-VCH: Weinheim, Germany, 2002; Chapter 7, pp 249-300.
16. For reviews on the 1,3-dipolar cycloaddition of nitrones, see: (a) Osborn, H. M.; Gemmell, N.; Harwood, L. M. J. Chem Soc., Perkin Trans. 1 2002, 2419-2438. (b) Frederickson, M. Teterahedron 1997, 53, 403-425. (c) Confalone, P. N.; Huie, E. M. Org. React. 1988, 36, 1-173. (d) Torseel, K. B. G. Nitrite Oxides, Nitrones and Nitronates in Organic synthesis; Feuer H., Ed.; VCH: Weinheim, Germany, 1988. (e) Ferrier, R. J.; Middleton, S. Chem. Rev. 1993, 93, 2779-2831. (f) Gothelf, K. V.; Jorgensen, K. A. Chem. Rev. 1998, 98, 8, 863-910. (g) Adams, J. P.; Box, D. S. J. Chem. Soc., Perkin Trans. 1 1999, 749-764. (h) Karlsson, S.; Hogberg, H. E. Org. Prep. Proced. Int. 2001, 33, 103-172. (i) Koumbis, A. E.; Gallos, J. K. Curr. Org. Chem. 2003, 7, 585-628. (j) Padwa, A.; Pearson, W. H. J. Nat. Prod. 2004, 67, 1074-1074. (k) Padwa, A.; Pearson, W. H. Org. Process Res. Dev. 2004, 8, 293-293. (1) Padwa, A.; Pearson, W. H. J. Am. Chem. Soc. 2002, 124, 12633-12634. (m) Cycloadditon Reactions in Organic synthesis; Carruthers, W., Ed.; Tetrahedron organic chemistry series; Pergamon Press: New York, 1990; Vol. 8, pp 269-314. (n) Advances in Cycloaddition; Curran, D. P., Ed.; JAI Press: London, UK, 1988, Vol. 1; 1990, Vol. 2; 1993, Vol. 3. (o) Gothelf, K. V. In Cycloaddition reactions in organic synthesis; Kobayashi, S., Jorgensen, K. A., Eds.; Wiley-VCH;, Weinheim, Germany, 2002; Chapter 6, pp 211-247. (p) Kanemasa, S. In Cycloaddition reactions in Organic synthesis; Kobayashi, S., Jorgensen, K. A., Eds.; Wiley-VCH: Weinheim, Germany, 2002; Chapter 7, pp 249-300.
17. For reviews on the 1,3-dipolar cycloaddition of nitrones, see: (a) Osborn, H. M.; Gemmell, N.; Harwood, L. M. J. Chem Soc., Perkin Trans. 1 2002, 2419-2438. (b) Frederickson, M. Teterahedron 1997, 53, 403-425. (c) Confalone, P. N.; Huie, E. M. Org. React. 1988, 36, 1-173. (d) Torseel, K. B. G. Nitrite Oxides, Nitrones and Nitronates in Organic synthesis; Feuer H., Ed.; VCH: Weinheim, Germany, 1988. (e) Ferrier, R. J.; Middleton, S. Chem. Rev. 1993, 93, 2779-2831. (f) Gothelf, K. V.; Jorgensen, K. A. Chem. Rev. 1998, 98, 8, 863-910. (g) Adams, J. P.; Box, D. S. J. Chem. Soc., Perkin Trans. 1 1999, 749-764. (h) Karlsson, S.; Hogberg, H. E. Org. Prep. Proced. Int. 2001, 33, 103-172. (i) Koumbis, A. E.; Gallos, J. K. Curr. Org. Chem. 2003, 7, 585-628. (j) Padwa, A.; Pearson, W. H. J. Nat. Prod. 2004, 67, 1074-1074. (k) Padwa, A.; Pearson, W. H. Org. Process Res. Dev. 2004, 8, 293-293. (1) Padwa, A.; Pearson, W. H. J. Am. Chem. Soc. 2002, 124, 12633-12634. (m) Cycloadditon Reactions in Organic synthesis; Carruthers, W., Ed.; Tetrahedron organic chemistry series; Pergamon Press: New York, 1990; Vol. 8, pp 269-314. (n) Advances in Cycloaddition; Curran, D. P., Ed.; JAI Press: London, UK, 1988, Vol. 1; 1990, Vol. 2; 1993, Vol. 3. (o) Gothelf, K. V. In Cycloaddition reactions in organic synthesis; Kobayashi, S., Jorgensen, K. A., Eds.; Wiley-VCH;, Weinheim, Germany, 2002; Chapter 6, pp 211-247. (p) Kanemasa, S. In Cycloaddition reactions in Organic synthesis; Kobayashi, S., Jorgensen, K. A., Eds.; Wiley-VCH: Weinheim, Germany, 2002; Chapter 7, pp 249-300.
18. For reviews on the 1,3-dipolar cycloaddition of nitrones, see: (a) Osborn, H. M.; Gemmell, N.; Harwood, L. M. J. Chem Soc., Perkin Trans. 1 2002, 2419-2438. (b) Frederickson, M. Teterahedron 1997, 53, 403-425. (c) Confalone, P. N.; Huie, E. M. Org. React. 1988, 36, 1-173. (d) Torseel, K. B. G. Nitrite Oxides, Nitrones and Nitronates in Organic synthesis; Feuer H., Ed.; VCH: Weinheim, Germany, 1988. (e) Ferrier, R. J.; Middleton, S. Chem. Rev. 1993, 93, 2779-2831. (f) Gothelf, K. V.; Jorgensen, K. A. Chem. Rev. 1998, 98, 8, 863-910. (g) Adams, J. P.; Box, D. S. J. Chem. Soc., Perkin Trans. 1 1999, 749-764. (h) Karlsson, S.; Hogberg, H. E. Org. Prep. Proced. Int. 2001, 33, 103-172. (i) Koumbis, A. E.; Gallos, J. K. Curr. Org. Chem. 2003, 7, 585-628. (j) Padwa, A.; Pearson, W. H. J. Nat. Prod. 2004, 67, 1074-1074. (k) Padwa, A.; Pearson, W. H. Org. Process Res. Dev. 2004, 8, 293-293. (1) Padwa, A.; Pearson, W. H. J. Am. Chem. Soc. 2002, 124, 12633-12634. (m) Cycloadditon Reactions in Organic synthesis; Carruthers, W., Ed.; Tetrahedron organic chemistry series; Pergamon Press: New York, 1990; Vol. 8, pp 269-314. (n) Advances in Cycloaddition; Curran, D. P., Ed.; JAI Press: London, UK, 1988, Vol. 1; 1990, Vol. 2; 1993, Vol. 3. (o) Gothelf, K. V. In Cycloaddition reactions in organic synthesis; Kobayashi, S., Jorgensen, K. A., Eds.; Wiley-VCH;, Weinheim, Germany, 2002; Chapter 6, pp 211-247. (p) Kanemasa, S. In Cycloaddition reactions in Organic synthesis; Kobayashi, S., Jorgensen, K. A., Eds.; Wiley-VCH: Weinheim, Germany, 2002; Chapter 7, pp 249-300.
19. For the synthetic applications of nitrones to azasugars, see: (a) Shimokawa, J.; Shirai, K.; Tanatani, A.; Hashimoto, Y.; Nagasawa, K. Angew. Chem. 2004, 43, 1559-1562. (b) Nagasawa, K.; Hashimoto, Y. Chem. Rec. 2003, 3, 201-211. (c) Torrente, S.; Noya, B.; Branchadell, V.; Alonso, R. J. Org. Chem. 2003, 68, 4772-4783. (d) Marco-Contelles, J.; Opazo, E. J. Carbohydr. Chem. 2002, 21, 201-218. (e) Cravotto, G.; Giovenzana, G. B.; Pilati, T.; Sisti, M.; Palmisano, G. J. Org. Chem. 2001, 66, 8447-8453. (f) Silva, A. M. G.; Tome, A. C.; Neves, M. G. P. M. S.; Silva, A. M. S.; Cavaleiro, J. A. S.; Perrone, D.; Dondoni, A. Tetrahedron Lett. 2002, 43, 603-605. (g) Gebarowski, P.; Sas, W. Chem. Commun. 2001, 915-916.
20. For the synthetic applications of nitrones to azasugars, see: (a) Shimokawa, J.; Shirai, K.; Tanatani, A.; Hashimoto, Y.; Nagasawa, K. Angew. Chem. 2004, 43, 1559-1562. (b) Nagasawa, K.; Hashimoto, Y. Chem. Rec. 2003, 3, 201-211. (c) Torrente, S.; Noya, B.; Branchadell, V.; Alonso, R. J. Org. Chem. 2003, 68, 4772-4783. (d) Marco-Contelles, J.; Opazo, E. J. Carbohydr. Chem. 2002, 21, 201-218. (e) Cravotto, G.; Giovenzana, G. B.; Pilati, T.; Sisti, M.; Palmisano, G. J. Org. Chem. 2001, 66, 8447-8453. (f) Silva, A. M. G.; Tome, A. C.; Neves, M. G. P. M. S.; Silva, A. M. S.; Cavaleiro, J. A. S.; Perrone, D.; Dondoni, A. Tetrahedron Lett. 2002, 43, 603-605. (g) Gebarowski, P.; Sas, W. Chem. Commun. 2001, 915-916.
21. For the synthetic applications of nitrones to azasugars, see: (a) Shimokawa, J.; Shirai, K.; Tanatani, A.; Hashimoto, Y.; Nagasawa, K. Angew. Chem. 2004, 43, 1559-1562. (b) Nagasawa, K.; Hashimoto, Y. Chem. Rec. 2003, 3, 201-211. (c) Torrente, S.; Noya, B.; Branchadell, V.; Alonso, R. J. Org. Chem. 2003, 68, 4772-4783. (d) Marco-Contelles, J.; Opazo, E. J. Carbohydr. Chem. 2002, 21, 201-218. (e) Cravotto, G.; Giovenzana, G. B.; Pilati, T.; Sisti, M.; Palmisano, G. J. Org. Chem. 2001, 66, 8447-8453. (f) Silva, A. M. G.; Tome, A. C.; Neves, M. G. P. M. S.; Silva, A. M. S.; Cavaleiro, J. A. S.; Perrone, D.; Dondoni, A. Tetrahedron Lett. 2002, 43, 603-605. (g) Gebarowski, P.; Sas, W. Chem. Commun. 2001, 915-916.
22. For the synthetic applications of nitrones to azasugars, see: (a) Shimokawa, J.; Shirai, K.; Tanatani, A.; Hashimoto, Y.; Nagasawa, K. Angew. Chem. 2004, 43, 1559-1562. (b) Nagasawa, K.; Hashimoto, Y. Chem. Rec. 2003, 3, 201-211. (c) Torrente, S.; Noya, B.; Branchadell, V.; Alonso, R. J. Org. Chem. 2003, 68, 4772-4783. (d) Marco-Contelles, J.; Opazo, E. J. Carbohydr. Chem. 2002, 21, 201-218. (e) Cravotto, G.; Giovenzana, G. B.; Pilati, T.; Sisti, M.; Palmisano, G. J. Org. Chem. 2001, 66, 8447-8453. (f) Silva, A. M. G.; Tome, A. C.; Neves, M. G. P. M. S.; Silva, A. M. S.; Cavaleiro, J. A. S.; Perrone, D.; Dondoni, A. Tetrahedron Lett. 2002, 43, 603-605. (g) Gebarowski, P.; Sas, W. Chem. Commun. 2001, 915-916.
23. For the synthetic applications of nitrones to azasugars, see: (a) Shimokawa, J.; Shirai, K.; Tanatani, A.; Hashimoto, Y.; Nagasawa, K. Angew. Chem. 2004, 43, 1559-1562. (b) Nagasawa, K.; Hashimoto, Y. Chem. Rec. 2003, 3, 201-211. (c) Torrente, S.; Noya, B.; Branchadell, V.; Alonso, R. J. Org. Chem. 2003, 68, 4772-4783. (d) Marco-Contelles, J.; Opazo, E. J. Carbohydr. Chem. 2002, 21, 201-218. (e) Cravotto, G.; Giovenzana, G. B.; Pilati, T.; Sisti, M.; Palmisano, G. J. Org. Chem. 2001, 66, 8447-8453. (f) Silva, A. M. G.; Tome, A. C.; Neves, M. G. P. M. S.; Silva, A. M. S.; Cavaleiro, J. A. S.; Perrone, D.; Dondoni, A. Tetrahedron Lett. 2002, 43, 603-605. (g) Gebarowski, P.; Sas, W. Chem. Commun. 2001, 915-916.
24. For the synthetic applications of nitrones to azasugars, see: (a) Shimokawa, J.; Shirai, K.; Tanatani, A.; Hashimoto, Y.; Nagasawa, K. Angew. Chem. 2004, 43, 1559-1562. (b) Nagasawa, K.; Hashimoto, Y. Chem. Rec. 2003, 3, 201-211. (c) Torrente, S.; Noya, B.; Branchadell, V.; Alonso, R. J. Org. Chem. 2003, 68, 4772-4783. (d) Marco-Contelles, J.; Opazo, E. J. Carbohydr. Chem. 2002, 21, 201-218. (e) Cravotto, G.; Giovenzana, G. B.; Pilati, T.; Sisti, M.; Palmisano, G. J. Org. Chem. 2001, 66, 8447-8453. (f) Silva, A. M. G.; Tome, A. C.; Neves, M. G. P. M. S.; Silva, A. M. S.; Cavaleiro, J. A. S.; Perrone, D.; Dondoni, A. Tetrahedron Lett. 2002, 43, 603-605. (g) Gebarowski, P.; Sas, W. Chem. Commun. 2001, 915-916.
25. For the synthetic applications of nitrones to azasugars, see: (a) Shimokawa, J.; Shirai, K.; Tanatani, A.; Hashimoto, Y.; Nagasawa, K. Angew. Chem. 2004, 43, 1559-1562. (b) Nagasawa, K.; Hashimoto, Y. Chem. Rec. 2003, 3, 201-211. (c) Torrente, S.; Noya, B.; Branchadell, V.; Alonso, R. J. Org. Chem. 2003, 68, 4772-4783. (d) Marco-Contelles, J.; Opazo, E. J. Carbohydr. Chem. 2002, 21, 201-218. (e) Cravotto, G.; Giovenzana, G. B.; Pilati, T.; Sisti, M.; Palmisano, G. J. Org. Chem. 2001, 66, 8447-8453. (f) Silva, A. M. G.; Tome, A. C.; Neves, M. G. P. M. S.; Silva, A. M. S.; Cavaleiro, J. A. S.; Perrone, D.; Dondoni, A. Tetrahedron Lett. 2002, 43, 603-605. (g) Gebarowski, P.; Sas, W. Chem. Commun. 2001, 915-916.
26. For nojirimycin, see: (a) Hughes, A. B.; Rudge, A. J. Nat. Prod. Rep. 1994, 11, 135-162. (b) Sears, P.; Wong, C, H. J. Chem. Soc., Chem. Commun. 1998, 1161-1170. (c) Butters, T. D.; Van den Brock, L. A. G. M.; Fleet, G. W. J.; Krulle, T. M.; Wormald, M. R.; Dwek, R. A.; Platt, F. M. Tetrahedron: Asymmetry 2000, 11, 113-124.
27. For nojirimycin, see: (a) Hughes, A. B.; Rudge, A. J. Nat. Prod. Rep. 1994, 11, 135-162. (b) Sears, P.; Wong, C, H. J. Chem. Soc., Chem. Commun. 1998, 1161-1170. (c) Butters, T. D.; Van den Brock, L. A. G. M.; Fleet, G. W. J.; Krulle, T. M.; Wormald, M. R.; Dwek, R. A.; Platt, F. M. Tetrahedron: Asymmetry 2000, 11, 113-124.
28. For nojirimycin, see: (a) Hughes, A. B.; Rudge, A. J. Nat. Prod. Rep. 1994, 11, 135-162. (b) Sears, P.; Wong, C, H. J. Chem. Soc., Chem. Commun. 1998, 1161-1170. (c) Butters, T. D.; Van den Brock, L. A. G. M.; Fleet, G. W. J.; Krulle, T. M.; Wormald, M. R.; Dwek, R. A.; Platt, F. M. Tetrahedron: Asymmetry 2000, 11, 113-124.
29. For castanospermine, see: (d) Elbein, A. D.; Molyneux, R. J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley-Interscience: New York, 1987; Vol. 5. Howard, A. S.; Michael, J. P. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1986; Vol. 28, Chapter 3. (e) Michael, J. P. Nat. Prod. Rep. 1990, 9, 485-523.
30. For castanospermine, see: (d) Elbein, A. D.; Molyneux, R. J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley-Interscience: New York, 1987; Vol. 5. Howard, A. S.; Michael, J. P. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1986; Vol. 28, Chapter 3. (e) Michael, J. P. Nat. Prod. Rep. 1990, 9, 485-523.
31. For castanospermine, see: (d) Elbein, A. D.; Molyneux, R. J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley-Interscience: New York, 1987; Vol. 5. Howard, A. S.; Michael, J. P. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1986; Vol. 28, Chapter 3. (e) Michael, J. P. Nat. Prod. Rep. 1990, 9, 485-523.
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60. 2 or TBDMSOTf (0.5 and 1.0 equiv), either in acetone or in dichloromethane at the elevated temperature, furnished a complex mixture of products, probably due to the cleavage of the 1,2-acetonoide group, thus precluding the use of Lewis acids in the 1,3-DC reaction of sugar nitrone.
61. 1a,f However since exo and endo are more correctly used for bicyclic systems, we have dropped this terminology as suggested by one of the referees. We are thankful to the referee for his comments.
62. The formation of keto product 7a obtained separately from 6a/ 6b was found to be identical on the basis of super imposable IR and other spectral and analytical data. Similarly, the keto product 7b derived from 6c/6d was found to be identical on the basis of mp, mixed mp, and super imposable IR and other spectral and analytical data.
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