A straightforward route to enantiopure pyrrolizidines and indolizidines by cycloaddition to pyrroline N-oxides derived from the chiral pool

Molecules

Volumn 4, Issue 1, 1999, Pages 1-12

  Goti, Andrea ^a   Cicchi, Stefano ^a   Cordero, Franca M ^a   Fedi, Valentina ^a   Brandi, Alberto ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

Author keywords

Cyclic nitrones; Glycosidase inhibitors; Pyrrolidines; Pyrrolizidines; Review; Stereoselective cycloaddition

Indexed keywords

AMINO ACID; ASPARTIC ACID; BUTENOLIDE; GLYCOSIDASE INHIBITOR; HASTANECINE; HYDROXYACID; INDOLIZIDINE ALKALOID; LENTIGINOSINE; MALEIC ACID DERIVATIVE; MALEIC ACID DIMETHYL ESTER; MALIC ACID; NITRONE DERIVATIVE; PYRROLIDINE DERIVATIVE; PYRROLINE DERIVATIVE; PYRROLIZIDINE ALKALOID; TARTARIC ACID; UNCLASSIFIED DRUG;

CHIRALITY; CYCLOADDITION; REVIEW;

EID: 0002213844     PISSN: 14203049     EISSN: None     Source Type: Journal    
DOI: 10.3390/40100001     Document Type: Review

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20. For some recent examples on the synthesis and use of different chiral, enantiomerically pure, endocyclic nitrones, see: (a) Golik, J.; Wong, H.; Krishnan, B.; Vyas, D. M.; Doyle, T. W. Tetrahedron Lett. 1991, 32, 1851-1854. (b) Tronchet, J. M. J.; Zosimo-Landolfo, G.; Balkadjian, M.; Ricca, A.; Zsély, M.; Barbalat-Rey, F.; Cabrini, D.; Lichtle, P.; Geoffroy, M. Tetrahedron Lett. 1991, 32, 4129-4132. (c) Grigg, R.; Markandu, J.; Perrior, T.; Surendrakumar, S.; Warnock, W. J. Tetrahedron 1992, 48, 6929-6952. (d) Herczegh, P.; Kovács, I.; Szilágyi, L.; Varga, T.; Dinya, T.; Sztaricskai, F. Tetrahedron Lett. 1993, 34, 1211-1214. (e) Berranger, T.; Langlois, Y. J. Org. Chem. 1995, 60, 1720-1726. (f) de March, P.; Figueredo, M.; Font, J.; Gallagher, T.; Milán, S. J. Chem. Soc., Chem. Commun. 1995, 2097-2098. (g) van den Broek, L. A. G. M. Tetrahedron 1996, 52, 4467-4478. (h) Ishikawa, T.; Tajima, Y.; Fukui, M.; Saito, S. Angew. Chem. Int. Ed. Engl. 1996, 35, 1863-1864. (i) Tamura, O.; Gotanda, K.; Terashima, R.; Kikuchi, M.; Miyawaki, T.; Sakamoto, M. J. Chem. Soc., Chem. Commun. 1996, 1861-1862. (j) Hall, A.; Meldrum, K. P.; Therond, P. R.; Wightman, R. H. Synlett 1997, 123-125. (k) Closa, M.; de March, P.; Figueredo, M.; Font, J. Tetrahedron: Asymmetry 1997, 8, 1031-1037. (l) Katagiri, N.; Okada, M.; Morishita, Y.; Kaneko, C. Tetrahedron 1997, 53, 5725-5746. (m) Chackalamannil, S.; Wang, Y. Tetrahedron 1997, 53, 11203-11210.
21. For some recent examples on the synthesis and use of different chiral, enantiomerically pure, endocyclic nitrones, see: (a) Golik, J.; Wong, H.; Krishnan, B.; Vyas, D. M.; Doyle, T. W. Tetrahedron Lett. 1991, 32, 1851-1854. (b) Tronchet, J. M. J.; Zosimo-Landolfo, G.; Balkadjian, M.; Ricca, A.; Zsély, M.; Barbalat-Rey, F.; Cabrini, D.; Lichtle, P.; Geoffroy, M. Tetrahedron Lett. 1991, 32, 4129-4132. (c) Grigg, R.; Markandu, J.; Perrior, T.; Surendrakumar, S.; Warnock, W. J. Tetrahedron 1992, 48, 6929-6952. (d) Herczegh, P.; Kovács, I.; Szilágyi, L.; Varga, T.; Dinya, T.; Sztaricskai, F. Tetrahedron Lett. 1993, 34, 1211-1214. (e) Berranger, T.; Langlois, Y. J. Org. Chem. 1995, 60, 1720-1726. (f) de March, P.; Figueredo, M.; Font, J.; Gallagher, T.; Milán, S. J. Chem. Soc., Chem. Commun. 1995, 2097-2098. (g) van den Broek, L. A. G. M. Tetrahedron 1996, 52, 4467-4478. (h) Ishikawa, T.; Tajima, Y.; Fukui, M.; Saito, S. Angew. Chem. Int. Ed. Engl. 1996, 35, 1863-1864. (i) Tamura, O.; Gotanda, K.; Terashima, R.; Kikuchi, M.; Miyawaki, T.; Sakamoto, M. J. Chem. Soc., Chem. Commun. 1996, 1861-1862. (j) Hall, A.; Meldrum, K. P.; Therond, P. R.; Wightman, R. H. Synlett 1997, 123-125. (k) Closa, M.; de March, P.; Figueredo, M.; Font, J. Tetrahedron: Asymmetry 1997, 8, 1031-1037. (l) Katagiri, N.; Okada, M.; Morishita, Y.; Kaneko, C. Tetrahedron 1997, 53, 5725-5746. (m) Chackalamannil, S.; Wang, Y. Tetrahedron 1997, 53, 11203-11210.
22. For some recent examples on the synthesis and use of different chiral, enantiomerically pure, endocyclic nitrones, see: (a) Golik, J.; Wong, H.; Krishnan, B.; Vyas, D. M.; Doyle, T. W. Tetrahedron Lett. 1991, 32, 1851-1854. (b) Tronchet, J. M. J.; Zosimo-Landolfo, G.; Balkadjian, M.; Ricca, A.; Zsély, M.; Barbalat-Rey, F.; Cabrini, D.; Lichtle, P.; Geoffroy, M. Tetrahedron Lett. 1991, 32, 4129-4132. (c) Grigg, R.; Markandu, J.; Perrior, T.; Surendrakumar, S.; Warnock, W. J. Tetrahedron 1992, 48, 6929-6952. (d) Herczegh, P.; Kovács, I.; Szilágyi, L.; Varga, T.; Dinya, T.; Sztaricskai, F. Tetrahedron Lett. 1993, 34, 1211-1214. (e) Berranger, T.; Langlois, Y. J. Org. Chem. 1995, 60, 1720-1726. (f) de March, P.; Figueredo, M.; Font, J.; Gallagher, T.; Milán, S. J. Chem. Soc., Chem. Commun. 1995, 2097-2098. (g) van den Broek, L. A. G. M. Tetrahedron 1996, 52, 4467-4478. (h) Ishikawa, T.; Tajima, Y.; Fukui, M.; Saito, S. Angew. Chem. Int. Ed. Engl. 1996, 35, 1863-1864. (i) Tamura, O.; Gotanda, K.; Terashima, R.; Kikuchi, M.; Miyawaki, T.; Sakamoto, M. J. Chem. Soc., Chem. Commun. 1996, 1861-1862. (j) Hall, A.; Meldrum, K. P.; Therond, P. R.; Wightman, R. H. Synlett 1997, 123-125. (k) Closa, M.; de March, P.; Figueredo, M.; Font, J. Tetrahedron: Asymmetry 1997, 8, 1031-1037. (l) Katagiri, N.; Okada, M.; Morishita, Y.; Kaneko, C. Tetrahedron 1997, 53, 5725-5746. (m) Chackalamannil, S.; Wang, Y. Tetrahedron 1997, 53, 11203-11210.
23. For some recent examples on the synthesis and use of different chiral, enantiomerically pure, endocyclic nitrones, see: (a) Golik, J.; Wong, H.; Krishnan, B.; Vyas, D. M.; Doyle, T. W. Tetrahedron Lett. 1991, 32, 1851-1854. (b) Tronchet, J. M. J.; Zosimo-Landolfo, G.; Balkadjian, M.; Ricca, A.; Zsély, M.; Barbalat-Rey, F.; Cabrini, D.; Lichtle, P.; Geoffroy, M. Tetrahedron Lett. 1991, 32, 4129-4132. (c) Grigg, R.; Markandu, J.; Perrior, T.; Surendrakumar, S.; Warnock, W. J. Tetrahedron 1992, 48, 6929-6952. (d) Herczegh, P.; Kovács, I.; Szilágyi, L.; Varga, T.; Dinya, T.; Sztaricskai, F. Tetrahedron Lett. 1993, 34, 1211-1214. (e) Berranger, T.; Langlois, Y. J. Org. Chem. 1995, 60, 1720-1726. (f) de March, P.; Figueredo, M.; Font, J.; Gallagher, T.; Milán, S. J. Chem. Soc., Chem. Commun. 1995, 2097-2098. (g) van den Broek, L. A. G. M. Tetrahedron 1996, 52, 4467-4478. (h) Ishikawa, T.; Tajima, Y.; Fukui, M.; Saito, S. Angew. Chem. Int. Ed. Engl. 1996, 35, 1863-1864. (i) Tamura, O.; Gotanda, K.; Terashima, R.; Kikuchi, M.; Miyawaki, T.; Sakamoto, M. J. Chem. Soc., Chem. Commun. 1996, 1861-1862. (j) Hall, A.; Meldrum, K. P.; Therond, P. R.; Wightman, R. H. Synlett 1997, 123-125. (k) Closa, M.; de March, P.; Figueredo, M.; Font, J. Tetrahedron: Asymmetry 1997, 8, 1031-1037. (l) Katagiri, N.; Okada, M.; Morishita, Y.; Kaneko, C. Tetrahedron 1997, 53, 5725-5746. (m) Chackalamannil, S.; Wang, Y. Tetrahedron 1997, 53, 11203-11210.
24. For some recent examples on the synthesis and use of different chiral, enantiomerically pure, endocyclic nitrones, see: (a) Golik, J.; Wong, H.; Krishnan, B.; Vyas, D. M.; Doyle, T. W. Tetrahedron Lett. 1991, 32, 1851-1854. (b) Tronchet, J. M. J.; Zosimo-Landolfo, G.; Balkadjian, M.; Ricca, A.; Zsély, M.; Barbalat-Rey, F.; Cabrini, D.; Lichtle, P.; Geoffroy, M. Tetrahedron Lett. 1991, 32, 4129-4132. (c) Grigg, R.; Markandu, J.; Perrior, T.; Surendrakumar, S.; Warnock, W. J. Tetrahedron 1992, 48, 6929-6952. (d) Herczegh, P.; Kovács, I.; Szilágyi, L.; Varga, T.; Dinya, T.; Sztaricskai, F. Tetrahedron Lett. 1993, 34, 1211-1214. (e) Berranger, T.; Langlois, Y. J. Org. Chem. 1995, 60, 1720-1726. (f) de March, P.; Figueredo, M.; Font, J.; Gallagher, T.; Milán, S. J. Chem. Soc., Chem. Commun. 1995, 2097-2098. (g) van den Broek, L. A. G. M. Tetrahedron 1996, 52, 4467-4478. (h) Ishikawa, T.; Tajima, Y.; Fukui, M.; Saito, S. Angew. Chem. Int. Ed. Engl. 1996, 35, 1863-1864. (i) Tamura, O.; Gotanda, K.; Terashima, R.; Kikuchi, M.; Miyawaki, T.; Sakamoto, M. J. Chem. Soc., Chem. Commun. 1996, 1861-1862. (j) Hall, A.; Meldrum, K. P.; Therond, P. R.; Wightman, R. H. Synlett 1997, 123-125. (k) Closa, M.; de March, P.; Figueredo, M.; Font, J. Tetrahedron: Asymmetry 1997, 8, 1031-1037. (l) Katagiri, N.; Okada, M.; Morishita, Y.; Kaneko, C. Tetrahedron 1997, 53, 5725-5746. (m) Chackalamannil, S.; Wang, Y. Tetrahedron 1997, 53, 11203-11210.
25. For some recent examples on the synthesis and use of different chiral, enantiomerically pure, endocyclic nitrones, see: (a) Golik, J.; Wong, H.; Krishnan, B.; Vyas, D. M.; Doyle, T. W. Tetrahedron Lett. 1991, 32, 1851-1854. (b) Tronchet, J. M. J.; Zosimo-Landolfo, G.; Balkadjian, M.; Ricca, A.; Zsély, M.; Barbalat-Rey, F.; Cabrini, D.; Lichtle, P.; Geoffroy, M. Tetrahedron Lett. 1991, 32, 4129-4132. (c) Grigg, R.; Markandu, J.; Perrior, T.; Surendrakumar, S.; Warnock, W. J. Tetrahedron 1992, 48, 6929-6952. (d) Herczegh, P.; Kovács, I.; Szilágyi, L.; Varga, T.; Dinya, T.; Sztaricskai, F. Tetrahedron Lett. 1993, 34, 1211-1214. (e) Berranger, T.; Langlois, Y. J. Org. Chem. 1995, 60, 1720-1726. (f) de March, P.; Figueredo, M.; Font, J.; Gallagher, T.; Milán, S. J. Chem. Soc., Chem. Commun. 1995, 2097-2098. (g) van den Broek, L. A. G. M. Tetrahedron 1996, 52, 4467-4478. (h) Ishikawa, T.; Tajima, Y.; Fukui, M.; Saito, S. Angew. Chem. Int. Ed. Engl. 1996, 35, 1863-1864. (i) Tamura, O.; Gotanda, K.; Terashima, R.; Kikuchi, M.; Miyawaki, T.; Sakamoto, M. J. Chem. Soc., Chem. Commun. 1996, 1861-1862. (j) Hall, A.; Meldrum, K. P.; Therond, P. R.; Wightman, R. H. Synlett 1997, 123-125. (k) Closa, M.; de March, P.; Figueredo, M.; Font, J. Tetrahedron: Asymmetry 1997, 8, 1031-1037. (l) Katagiri, N.; Okada, M.; Morishita, Y.; Kaneko, C. Tetrahedron 1997, 53, 5725-5746. (m) Chackalamannil, S.; Wang, Y. Tetrahedron 1997, 53, 11203-11210.
26. For some recent examples on the synthesis and use of different chiral, enantiomerically pure, endocyclic nitrones, see: (a) Golik, J.; Wong, H.; Krishnan, B.; Vyas, D. M.; Doyle, T. W. Tetrahedron Lett. 1991, 32, 1851-1854. (b) Tronchet, J. M. J.; Zosimo-Landolfo, G.; Balkadjian, M.; Ricca, A.; Zsély, M.; Barbalat-Rey, F.; Cabrini, D.; Lichtle, P.; Geoffroy, M. Tetrahedron Lett. 1991, 32, 4129-4132. (c) Grigg, R.; Markandu, J.; Perrior, T.; Surendrakumar, S.; Warnock, W. J. Tetrahedron 1992, 48, 6929-6952. (d) Herczegh, P.; Kovács, I.; Szilágyi, L.; Varga, T.; Dinya, T.; Sztaricskai, F. Tetrahedron Lett. 1993, 34, 1211-1214. (e) Berranger, T.; Langlois, Y. J. Org. Chem. 1995, 60, 1720-1726. (f) de March, P.; Figueredo, M.; Font, J.; Gallagher, T.; Milán, S. J. Chem. Soc., Chem. Commun. 1995, 2097-2098. (g) van den Broek, L. A. G. M. Tetrahedron 1996, 52, 4467-4478. (h) Ishikawa, T.; Tajima, Y.; Fukui, M.; Saito, S. Angew. Chem. Int. Ed. Engl. 1996, 35, 1863-1864. (i) Tamura, O.; Gotanda, K.; Terashima, R.; Kikuchi, M.; Miyawaki, T.; Sakamoto, M. J. Chem. Soc., Chem. Commun. 1996, 1861-1862. (j) Hall, A.; Meldrum, K. P.; Therond, P. R.; Wightman, R. H. Synlett 1997, 123-125. (k) Closa, M.; de March, P.; Figueredo, M.; Font, J. Tetrahedron: Asymmetry 1997, 8, 1031-1037. (l) Katagiri, N.; Okada, M.; Morishita, Y.; Kaneko, C. Tetrahedron 1997, 53, 5725-5746. (m) Chackalamannil, S.; Wang, Y. Tetrahedron 1997, 53, 11203-11210.
27. For some recent examples on the synthesis and use of different chiral, enantiomerically pure, endocyclic nitrones, see: (a) Golik, J.; Wong, H.; Krishnan, B.; Vyas, D. M.; Doyle, T. W. Tetrahedron Lett. 1991, 32, 1851-1854. (b) Tronchet, J. M. J.; Zosimo-Landolfo, G.; Balkadjian, M.; Ricca, A.; Zsély, M.; Barbalat-Rey, F.; Cabrini, D.; Lichtle, P.; Geoffroy, M. Tetrahedron Lett. 1991, 32, 4129-4132. (c) Grigg, R.; Markandu, J.; Perrior, T.; Surendrakumar, S.; Warnock, W. J. Tetrahedron 1992, 48, 6929-6952. (d) Herczegh, P.; Kovács, I.; Szilágyi, L.; Varga, T.; Dinya, T.; Sztaricskai, F. Tetrahedron Lett. 1993, 34, 1211-1214. (e) Berranger, T.; Langlois, Y. J. Org. Chem. 1995, 60, 1720-1726. (f) de March, P.; Figueredo, M.; Font, J.; Gallagher, T.; Milán, S. J. Chem. Soc., Chem. Commun. 1995, 2097-2098. (g) van den Broek, L. A. G. M. Tetrahedron 1996, 52, 4467-4478. (h) Ishikawa, T.; Tajima, Y.; Fukui, M.; Saito, S. Angew. Chem. Int. Ed. Engl. 1996, 35, 1863-1864. (i) Tamura, O.; Gotanda, K.; Terashima, R.; Kikuchi, M.; Miyawaki, T.; Sakamoto, M. J. Chem. Soc., Chem. Commun. 1996, 1861-1862. (j) Hall, A.; Meldrum, K. P.; Therond, P. R.; Wightman, R. H. Synlett 1997, 123-125. (k) Closa, M.; de March, P.; Figueredo, M.; Font, J. Tetrahedron: Asymmetry 1997, 8, 1031-1037. (l) Katagiri, N.; Okada, M.; Morishita, Y.; Kaneko, C. Tetrahedron 1997, 53, 5725-5746. (m) Chackalamannil, S.; Wang, Y. Tetrahedron 1997, 53, 11203-11210.
28. For some recent examples on the synthesis and use of different chiral, enantiomerically pure, endocyclic nitrones, see: (a) Golik, J.; Wong, H.; Krishnan, B.; Vyas, D. M.; Doyle, T. W. Tetrahedron Lett. 1991, 32, 1851-1854. (b) Tronchet, J. M. J.; Zosimo-Landolfo, G.; Balkadjian, M.; Ricca, A.; Zsély, M.; Barbalat-Rey, F.; Cabrini, D.; Lichtle, P.; Geoffroy, M. Tetrahedron Lett. 1991, 32, 4129-4132. (c) Grigg, R.; Markandu, J.; Perrior, T.; Surendrakumar, S.; Warnock, W. J. Tetrahedron 1992, 48, 6929-6952. (d) Herczegh, P.; Kovács, I.; Szilágyi, L.; Varga, T.; Dinya, T.; Sztaricskai, F. Tetrahedron Lett. 1993, 34, 1211-1214. (e) Berranger, T.; Langlois, Y. J. Org. Chem. 1995, 60, 1720-1726. (f) de March, P.; Figueredo, M.; Font, J.; Gallagher, T.; Milán, S. J. Chem. Soc., Chem. Commun. 1995, 2097-2098. (g) van den Broek, L. A. G. M. Tetrahedron 1996, 52, 4467-4478. (h) Ishikawa, T.; Tajima, Y.; Fukui, M.; Saito, S. Angew. Chem. Int. Ed. Engl. 1996, 35, 1863-1864. (i) Tamura, O.; Gotanda, K.; Terashima, R.; Kikuchi, M.; Miyawaki, T.; Sakamoto, M. J. Chem. Soc., Chem. Commun. 1996, 1861-1862. (j) Hall, A.; Meldrum, K. P.; Therond, P. R.; Wightman, R. H. Synlett 1997, 123-125. (k) Closa, M.; de March, P.; Figueredo, M.; Font, J. Tetrahedron: Asymmetry 1997, 8, 1031-1037. (l) Katagiri, N.; Okada, M.; Morishita, Y.; Kaneko, C. Tetrahedron 1997, 53, 5725-5746. (m) Chackalamannil, S.; Wang, Y. Tetrahedron 1997, 53, 11203-11210.
29. For some recent examples on the synthesis and use of different chiral, enantiomerically pure, endocyclic nitrones, see: (a) Golik, J.; Wong, H.; Krishnan, B.; Vyas, D. M.; Doyle, T. W. Tetrahedron Lett. 1991, 32, 1851-1854. (b) Tronchet, J. M. J.; Zosimo-Landolfo, G.; Balkadjian, M.; Ricca, A.; Zsély, M.; Barbalat-Rey, F.; Cabrini, D.; Lichtle, P.; Geoffroy, M. Tetrahedron Lett. 1991, 32, 4129-4132. (c) Grigg, R.; Markandu, J.; Perrior, T.; Surendrakumar, S.; Warnock, W. J. Tetrahedron 1992, 48, 6929-6952. (d) Herczegh, P.; Kovács, I.; Szilágyi, L.; Varga, T.; Dinya, T.; Sztaricskai, F. Tetrahedron Lett. 1993, 34, 1211-1214. (e) Berranger, T.; Langlois, Y. J. Org. Chem. 1995, 60, 1720-1726. (f) de March, P.; Figueredo, M.; Font, J.; Gallagher, T.; Milán, S. J. Chem. Soc., Chem. Commun. 1995, 2097-2098. (g) van den Broek, L. A. G. M. Tetrahedron 1996, 52, 4467-4478. (h) Ishikawa, T.; Tajima, Y.; Fukui, M.; Saito, S. Angew. Chem. Int. Ed. Engl. 1996, 35, 1863-1864. (i) Tamura, O.; Gotanda, K.; Terashima, R.; Kikuchi, M.; Miyawaki, T.; Sakamoto, M. J. Chem. Soc., Chem. Commun. 1996, 1861-1862. (j) Hall, A.; Meldrum, K. P.; Therond, P. R.; Wightman, R. H. Synlett 1997, 123-125. (k) Closa, M.; de March, P.; Figueredo, M.; Font, J. Tetrahedron: Asymmetry 1997, 8, 1031-1037. (l) Katagiri, N.; Okada, M.; Morishita, Y.; Kaneko, C. Tetrahedron 1997, 53, 5725-5746. (m) Chackalamannil, S.; Wang, Y. Tetrahedron 1997, 53, 11203-11210.
30. For some recent examples on the synthesis and use of different chiral, enantiomerically pure, endocyclic nitrones, see: (a) Golik, J.; Wong, H.; Krishnan, B.; Vyas, D. M.; Doyle, T. W. Tetrahedron Lett. 1991, 32, 1851-1854. (b) Tronchet, J. M. J.; Zosimo-Landolfo, G.; Balkadjian, M.; Ricca, A.; Zsély, M.; Barbalat-Rey, F.; Cabrini, D.; Lichtle, P.; Geoffroy, M. Tetrahedron Lett. 1991, 32, 4129-4132. (c) Grigg, R.; Markandu, J.; Perrior, T.; Surendrakumar, S.; Warnock, W. J. Tetrahedron 1992, 48, 6929-6952. (d) Herczegh, P.; Kovács, I.; Szilágyi, L.; Varga, T.; Dinya, T.; Sztaricskai, F. Tetrahedron Lett. 1993, 34, 1211-1214. (e) Berranger, T.; Langlois, Y. J. Org. Chem. 1995, 60, 1720-1726. (f) de March, P.; Figueredo, M.; Font, J.; Gallagher, T.; Milán, S. J. Chem. Soc., Chem. Commun. 1995, 2097-2098. (g) van den Broek, L. A. G. M. Tetrahedron 1996, 52, 4467-4478. (h) Ishikawa, T.; Tajima, Y.; Fukui, M.; Saito, S. Angew. Chem. Int. Ed. Engl. 1996, 35, 1863-1864. (i) Tamura, O.; Gotanda, K.; Terashima, R.; Kikuchi, M.; Miyawaki, T.; Sakamoto, M. J. Chem. Soc., Chem. Commun. 1996, 1861-1862. (j) Hall, A.; Meldrum, K. P.; Therond, P. R.; Wightman, R. H. Synlett 1997, 123-125. (k) Closa, M.; de March, P.; Figueredo, M.; Font, J. Tetrahedron: Asymmetry 1997, 8, 1031-1037. (l) Katagiri, N.; Okada, M.; Morishita, Y.; Kaneko, C. Tetrahedron 1997, 53, 5725-5746. (m) Chackalamannil, S.; Wang, Y. Tetrahedron 1997, 53, 11203-11210.
31. For some recent examples on the synthesis and use of different chiral, enantiomerically pure, endocyclic nitrones, see: (a) Golik, J.; Wong, H.; Krishnan, B.; Vyas, D. M.; Doyle, T. W. Tetrahedron Lett. 1991, 32, 1851-1854. (b) Tronchet, J. M. J.; Zosimo-Landolfo, G.; Balkadjian, M.; Ricca, A.; Zsély, M.; Barbalat-Rey, F.; Cabrini, D.; Lichtle, P.; Geoffroy, M. Tetrahedron Lett. 1991, 32, 4129-4132. (c) Grigg, R.; Markandu, J.; Perrior, T.; Surendrakumar, S.; Warnock, W. J. Tetrahedron 1992, 48, 6929-6952. (d) Herczegh, P.; Kovács, I.; Szilágyi, L.; Varga, T.; Dinya, T.; Sztaricskai, F. Tetrahedron Lett. 1993, 34, 1211-1214. (e) Berranger, T.; Langlois, Y. J. Org. Chem. 1995, 60, 1720-1726. (f) de March, P.; Figueredo, M.; Font, J.; Gallagher, T.; Milán, S. J. Chem. Soc., Chem. Commun. 1995, 2097-2098. (g) van den Broek, L. A. G. M. Tetrahedron 1996, 52, 4467-4478. (h) Ishikawa, T.; Tajima, Y.; Fukui, M.; Saito, S. Angew. Chem. Int. Ed. Engl. 1996, 35, 1863-1864. (i) Tamura, O.; Gotanda, K.; Terashima, R.; Kikuchi, M.; Miyawaki, T.; Sakamoto, M. J. Chem. Soc., Chem. Commun. 1996, 1861-1862. (j) Hall, A.; Meldrum, K. P.; Therond, P. R.; Wightman, R. H. Synlett 1997, 123-125. (k) Closa, M.; de March, P.; Figueredo, M.; Font, J. Tetrahedron: Asymmetry 1997, 8, 1031-1037. (l) Katagiri, N.; Okada, M.; Morishita, Y.; Kaneko, C. Tetrahedron 1997, 53, 5725-5746. (m) Chackalamannil, S.; Wang, Y. Tetrahedron 1997, 53, 11203-11210.
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36. Reviews: (a) Elbein, A. D. Ann. Rev. Biochem. 1987, 56, 497-534. (b) Vogel, P. Chimica Oggi 1992, 10 (August-September), 9-15. (c) Winchester, B.; Fleet, G. W. J. Glycobiology 1992, 2, 199-210. (d) Legler, G. Adv. Carbohydr. Chem. Biochem. 1990, 48, 319-384. (e) Elbein, A. D.; Molyneux, R. J. In "Alkaloids: Chemical and Biological Perspectives"; Pelletier, S. W., Ed.; Wiley-Interscience: New York, 1987; vol. 5, ch. 1. (f) Howard, A. S.; Michael, J. P. In "The Alkaloids"; Brossi, A., Ed.; Academic Press: New York, 1986; vol. 28, ch. 3. (g) Cossy, J.; Vogel, P. In "Studies in Natural Product Chemistry"; Atta-ur-Rahman, Ed.; Elsevier: New York, 1993; vol. 12, p. 275.
37. Reviews: (a) Elbein, A. D. Ann. Rev. Biochem. 1987, 56, 497-534. (b) Vogel, P. Chimica Oggi 1992, 10 (August-September), 9-15. (c) Winchester, B.; Fleet, G. W. J. Glycobiology 1992, 2, 199-210. (d) Legler, G. Adv. Carbohydr. Chem. Biochem. 1990, 48, 319-384. (e) Elbein, A. D.; Molyneux, R. J. In "Alkaloids: Chemical and Biological Perspectives"; Pelletier, S. W., Ed.; Wiley-Interscience: New York, 1987; vol. 5, ch. 1. (f) Howard, A. S.; Michael, J. P. In "The Alkaloids"; Brossi, A., Ed.; Academic Press: New York, 1986; vol. 28, ch. 3. (g) Cossy, J.; Vogel, P. In "Studies in Natural Product Chemistry"; Atta-ur-Rahman, Ed.; Elsevier: New York, 1993; vol. 12, p. 275.
38. Reviews: (a) Elbein, A. D. Ann. Rev. Biochem. 1987, 56, 497-534. (b) Vogel, P. Chimica Oggi 1992, 10 (August-September), 9-15. (c) Winchester, B.; Fleet, G. W. J. Glycobiology 1992, 2, 199-210. (d) Legler, G. Adv. Carbohydr. Chem. Biochem. 1990, 48, 319-384. (e) Elbein, A. D.; Molyneux, R. J. In "Alkaloids: Chemical and Biological Perspectives"; Pelletier, S. W., Ed.; Wiley-Interscience: New York, 1987; vol. 5, ch. 1. (f) Howard, A. S.; Michael, J. P. In "The Alkaloids"; Brossi, A., Ed.; Academic Press: New York, 1986; vol. 28, ch. 3. (g) Cossy, J.; Vogel, P. In "Studies in Natural Product Chemistry"; Atta-ur-Rahman, Ed.; Elsevier: New York, 1993; vol. 12, p. 275.
39. Reviews: (a) Elbein, A. D. Ann. Rev. Biochem. 1987, 56, 497-534. (b) Vogel, P. Chimica Oggi 1992, 10 (August-September), 9-15. (c) Winchester, B.; Fleet, G. W. J. Glycobiology 1992, 2, 199-210. (d) Legler, G. Adv. Carbohydr. Chem. Biochem. 1990, 48, 319-384. (e) Elbein, A. D.; Molyneux, R. J. In "Alkaloids: Chemical and Biological Perspectives"; Pelletier, S. W., Ed.; Wiley-Interscience: New York, 1987; vol. 5, ch. 1. (f) Howard, A. S.; Michael, J. P. In "The Alkaloids"; Brossi, A., Ed.; Academic Press: New York, 1986; vol. 28, ch. 3. (g) Cossy, J.; Vogel, P. In "Studies in Natural Product Chemistry"; Atta-ur-Rahman, Ed.; Elsevier: New York, 1993; vol. 12, p. 275.
40. Reviews: (a) Elbein, A. D. Ann. Rev. Biochem. 1987, 56, 497-534. (b) Vogel, P. Chimica Oggi 1992, 10 (August-September), 9-15. (c) Winchester, B.; Fleet, G. W. J. Glycobiology 1992, 2, 199-210. (d) Legler, G. Adv. Carbohydr. Chem. Biochem. 1990, 48, 319-384. (e) Elbein, A. D.; Molyneux, R. J. In "Alkaloids: Chemical and Biological Perspectives"; Pelletier, S. W., Ed.; Wiley-Interscience: New York, 1987; vol. 5, ch. 1. (f) Howard, A. S.; Michael, J. P. In "The Alkaloids"; Brossi, A., Ed.; Academic Press: New York, 1986; vol. 28, ch. 3. (g) Cossy, J.; Vogel, P. In "Studies in Natural Product Chemistry"; Atta-ur-Rahman, Ed.; Elsevier: New York, 1993; vol. 12, p. 275.
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