Synthesis of (3S,4R)-3,4-isopropylidenedioxy-1-pyrroline-N-oxide, an enantiopure functionalized cyclic nitrone; cycloaddition reactions with dimethyl maleate and dimethyl fumarate

Synthetic Communications

Volumn 28, Issue 18, 1998, Pages 3443-3450

  Closa, Montserrat ^a,b   Wightman, Richard H ^a  

^a HERIOT WATT UNIVERSITY   (United Kingdom)

^b UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

3,4 ISOPROPYLIDENEDIOXY 1 PYRROLINE N OXIDE; AUSTRALINE; CASTANOSPERMINE; FUMARIC ACID DIMETHYL ESTER; GLYCOSIDASE; MALEIC ACID DIMETHYL ESTER; PYRROLIZIDINE; SWAINSONINE; UNCLASSIFIED DRUG;

ARTICLE; COLUMN CHROMATOGRAPHY; ENANTIOMER; ENZYME ACTIVITY; ENZYME INHIBITION; STEREOCHEMISTRY; STEREOISOMERISM;

EID: 0031782230     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919808004452     Document Type: Article

References (26)

1. Synthesis of castanospermine and isomers: Burgess, K.; Henderson, I. Tetrahedron 1992, 48, 4045 and refs. therein; synthesis of hydroxylated indolizidines: Herczegh, P.; Kovács, I.; Sztaricskai, F. in Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products; Lucacs, G., Ed.; Springer Verlag: Berlin, 1993; p. 751.
2. Synthesis of castanospermine and isomers: Burgess, K.; Henderson, I. Tetrahedron 1992, 48, 4045 and refs. therein; synthesis of hydroxylated indolizidines: Herczegh, P.; Kovács, I.; Sztaricskai, F. in Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products; Lucacs, G., Ed.; Springer Verlag: Berlin, 1993; p. 751.
3. Pearson, W.H.; Hines, J.V. Tetrahedron Lett., 1991, 32, 5513; Choi, S., Bruce, I.; Fairbanks, A.J.; Fleet, G.W.J.; Jones, A.H.; Nash, R.J.; Fellows. L.E. Tetrahedron Lett., 1991, 32, 5517, and refs. therein.
4. Pearson, W.H.; Hines, J.V. Tetrahedron Lett., 1991, 32, 5513; Choi, S., Bruce, I.; Fairbanks, A.J.; Fleet, G.W.J.; Jones, A.H.; Nash, R.J.; Fellows. L.E. Tetrahedron Lett., 1991, 32, 5517, and refs. therein.
5. Winchester, B.; Fleet, G. W. J. Glycobiology 1992, 2, 199.
6. For the preparation and use in cycloadditions of enantiopure 1-pyrroline-N-oxides (five-ring cyclic nitrones) with (protected) hydroxy and hydroxy-methyl substituents, see: (a) Golik, J.; Wong, H.; Krishnan, B.; Vyas, D.M.; Doyle, T.W. Tetrahedron Lett., 1991, 32, 1851; (b) Ballini, R.; Marcantoni, E.; Petrini, M. J. Org. Chem., 1992, 57, 1316; (c) McCaig, A.E.; Wightman, R.H. Tetrahedron Lett., 1993, 34, 3939; (d) Cicchi, S.; Höld, I.; Brandi, A. J. Org. Chem., 1993, 58, 5274; (e) Cicchi, S.; Goti, A.; Brandi, A. J. Org. Chem., 1995, 60, 4743; (f) de March, P.; Figueredo, M.; Font, J.; Gallagher, T.; Milán, S. J. Chem. Soc., Chem. Commun., 1995, 2097; (g) Brandi, A.; Cicchi, S.; Cordera, F.M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem., 1995, 60, 6806; (h) Goti, A.; Cardona, F.; Brandi, A. Synlett, 1996, 761; (i) Ishikawa, T.; Tajima, Y.; Fukui, M.; Saito, S. Angew. Chem., Int. Ed. Engl., 1996, 35, 1863; (j) Goti, A.; Cardona, F. Brandi, A.; Picasso, S.; Vogel, P. Tetrahedron: Asymm., 1996, 7, 1659; (k) Hall, A.; Meldrum, K.P.; Therond, P.R.; Wightman, R.H. Synlett, 1997, 123; (l) Goti, A.; Cicchi, S.; Fedi, V.; Nannelli, L.; Brandi, A. J. Org. Chem., 1997, 62, 3119; (m) Closa, M.; de March, P.; Figueredo, M.; Font, J. Tetrahedron: Asymm., 1997, 8, 1031; (n) Goti, A.; Fedi, V.; Nannelli, L.; De Sarlo, F.; Brandi, A. Synlett, 1997, 577.
7. For the preparation and use in cycloadditions of enantiopure 1-pyrroline-N-oxides (five-ring cyclic nitrones) with (protected) hydroxy and hydroxy-methyl substituents, see: (a) Golik, J.; Wong, H.; Krishnan, B.; Vyas, D.M.; Doyle, T.W. Tetrahedron Lett., 1991, 32, 1851; (b) Ballini, R.; Marcantoni, E.; Petrini, M. J. Org. Chem., 1992, 57, 1316; (c) McCaig, A.E.; Wightman, R.H. Tetrahedron Lett., 1993, 34, 3939; (d) Cicchi, S.; Höld, I.; Brandi, A. J. Org. Chem., 1993, 58, 5274; (e) Cicchi, S.; Goti, A.; Brandi, A. J. Org. Chem., 1995, 60, 4743; (f) de March, P.; Figueredo, M.; Font, J.; Gallagher, T.; Milán, S. J. Chem. Soc., Chem. Commun., 1995, 2097; (g) Brandi, A.; Cicchi, S.; Cordera, F.M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem., 1995, 60, 6806; (h) Goti, A.; Cardona, F.; Brandi, A. Synlett, 1996, 761; (i) Ishikawa, T.; Tajima, Y.; Fukui, M.; Saito, S. Angew. Chem., Int. Ed. Engl., 1996, 35, 1863; (j) Goti, A.; Cardona, F. Brandi, A.; Picasso, S.; Vogel, P. Tetrahedron: Asymm., 1996, 7, 1659; (k) Hall, A.; Meldrum, K.P.; Therond, P.R.; Wightman, R.H. Synlett, 1997, 123; (l) Goti, A.; Cicchi, S.; Fedi, V.; Nannelli, L.; Brandi, A. J. Org. Chem., 1997, 62, 3119; (m) Closa, M.; de March, P.; Figueredo, M.; Font, J. Tetrahedron: Asymm., 1997, 8, 1031; (n) Goti, A.; Fedi, V.; Nannelli, L.; De Sarlo, F.; Brandi, A. Synlett, 1997, 577.
8. For the preparation and use in cycloadditions of enantiopure 1-pyrroline-N-oxides (five-ring cyclic nitrones) with (protected) hydroxy and hydroxy-methyl substituents, see: (a) Golik, J.; Wong, H.; Krishnan, B.; Vyas, D.M.; Doyle, T.W. Tetrahedron Lett., 1991, 32, 1851; (b) Ballini, R.; Marcantoni, E.; Petrini, M. J. Org. Chem., 1992, 57, 1316; (c) McCaig, A.E.; Wightman, R.H. Tetrahedron Lett., 1993, 34, 3939; (d) Cicchi, S.; Höld, I.; Brandi, A. J. Org. Chem., 1993, 58, 5274; (e) Cicchi, S.; Goti, A.; Brandi, A. J. Org. Chem., 1995, 60, 4743; (f) de March, P.; Figueredo, M.; Font, J.; Gallagher, T.; Milán, S. J. Chem. Soc., Chem. Commun., 1995, 2097; (g) Brandi, A.; Cicchi, S.; Cordera, F.M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem., 1995, 60, 6806; (h) Goti, A.; Cardona, F.; Brandi, A. Synlett, 1996, 761; (i) Ishikawa, T.; Tajima, Y.; Fukui, M.; Saito, S. Angew. Chem., Int. Ed. Engl., 1996, 35, 1863; (j) Goti, A.; Cardona, F. Brandi, A.; Picasso, S.; Vogel, P. Tetrahedron: Asymm., 1996, 7, 1659; (k) Hall, A.; Meldrum, K.P.; Therond, P.R.; Wightman, R.H. Synlett, 1997, 123; (l) Goti, A.; Cicchi, S.; Fedi, V.; Nannelli, L.; Brandi, A. J. Org. Chem., 1997, 62, 3119; (m) Closa, M.; de March, P.; Figueredo, M.; Font, J. Tetrahedron: Asymm., 1997, 8, 1031; (n) Goti, A.; Fedi, V.; Nannelli, L.; De Sarlo, F.; Brandi, A. Synlett, 1997, 577.
9. For the preparation and use in cycloadditions of enantiopure 1-pyrroline-N-oxides (five-ring cyclic nitrones) with (protected) hydroxy and hydroxy-methyl substituents, see: (a) Golik, J.; Wong, H.; Krishnan, B.; Vyas, D.M.; Doyle, T.W. Tetrahedron Lett., 1991, 32, 1851; (b) Ballini, R.; Marcantoni, E.; Petrini, M. J. Org. Chem., 1992, 57, 1316; (c) McCaig, A.E.; Wightman, R.H. Tetrahedron Lett., 1993, 34, 3939; (d) Cicchi, S.; Höld, I.; Brandi, A. J. Org. Chem., 1993, 58, 5274; (e) Cicchi, S.; Goti, A.; Brandi, A. J. Org. Chem., 1995, 60, 4743; (f) de March, P.; Figueredo, M.; Font, J.; Gallagher, T.; Milán, S. J. Chem. Soc., Chem. Commun., 1995, 2097; (g) Brandi, A.; Cicchi, S.; Cordera, F.M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem., 1995, 60, 6806; (h) Goti, A.; Cardona, F.; Brandi, A. Synlett, 1996, 761; (i) Ishikawa, T.; Tajima, Y.; Fukui, M.; Saito, S. Angew. Chem., Int. Ed. Engl., 1996, 35, 1863; (j) Goti, A.; Cardona, F. Brandi, A.; Picasso, S.; Vogel, P. Tetrahedron: Asymm., 1996, 7, 1659; (k) Hall, A.; Meldrum, K.P.; Therond, P.R.; Wightman, R.H. Synlett, 1997, 123; (l) Goti, A.; Cicchi, S.; Fedi, V.; Nannelli, L.; Brandi, A. J. Org. Chem., 1997, 62, 3119; (m) Closa, M.; de March, P.; Figueredo, M.; Font, J. Tetrahedron: Asymm., 1997, 8, 1031; (n) Goti, A.; Fedi, V.; Nannelli, L.; De Sarlo, F.; Brandi, A. Synlett, 1997, 577.
10. For the preparation and use in cycloadditions of enantiopure 1-pyrroline-N-oxides (five-ring cyclic nitrones) with (protected) hydroxy and hydroxy-methyl substituents, see: (a) Golik, J.; Wong, H.; Krishnan, B.; Vyas, D.M.; Doyle, T.W. Tetrahedron Lett., 1991, 32, 1851; (b) Ballini, R.; Marcantoni, E.; Petrini, M. J. Org. Chem., 1992, 57, 1316; (c) McCaig, A.E.; Wightman, R.H. Tetrahedron Lett., 1993, 34, 3939; (d) Cicchi, S.; Höld, I.; Brandi, A. J. Org. Chem., 1993, 58, 5274; (e) Cicchi, S.; Goti, A.; Brandi, A. J. Org. Chem., 1995, 60, 4743; (f) de March, P.; Figueredo, M.; Font, J.; Gallagher, T.; Milán, S. J. Chem. Soc., Chem. Commun., 1995, 2097; (g) Brandi, A.; Cicchi, S.; Cordera, F.M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem., 1995, 60, 6806; (h) Goti, A.; Cardona, F.; Brandi, A. Synlett, 1996, 761; (i) Ishikawa, T.; Tajima, Y.; Fukui, M.; Saito, S. Angew. Chem., Int. Ed. Engl., 1996, 35, 1863; (j) Goti, A.; Cardona, F. Brandi, A.; Picasso, S.; Vogel, P. Tetrahedron: Asymm., 1996, 7, 1659; (k) Hall, A.; Meldrum, K.P.; Therond, P.R.; Wightman, R.H. Synlett, 1997, 123; (l) Goti, A.; Cicchi, S.; Fedi, V.; Nannelli, L.; Brandi, A. J. Org. Chem., 1997, 62, 3119; (m) Closa, M.; de March, P.; Figueredo, M.; Font, J. Tetrahedron: Asymm., 1997, 8, 1031; (n) Goti, A.; Fedi, V.; Nannelli, L.; De Sarlo, F.; Brandi, A. Synlett, 1997, 577.
11. For the preparation and use in cycloadditions of enantiopure 1-pyrroline-N-oxides (five-ring cyclic nitrones) with (protected) hydroxy and hydroxy-methyl substituents, see: (a) Golik, J.; Wong, H.; Krishnan, B.; Vyas, D.M.; Doyle, T.W. Tetrahedron Lett., 1991, 32, 1851; (b) Ballini, R.; Marcantoni, E.; Petrini, M. J. Org. Chem., 1992, 57, 1316; (c) McCaig, A.E.; Wightman, R.H. Tetrahedron Lett., 1993, 34, 3939; (d) Cicchi, S.; Höld, I.; Brandi, A. J. Org. Chem., 1993, 58, 5274; (e) Cicchi, S.; Goti, A.; Brandi, A. J. Org. Chem., 1995, 60, 4743; (f) de March, P.; Figueredo, M.; Font, J.; Gallagher, T.; Milán, S. J. Chem. Soc., Chem. Commun., 1995, 2097; (g) Brandi, A.; Cicchi, S.; Cordera, F.M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem., 1995, 60, 6806; (h) Goti, A.; Cardona, F.; Brandi, A. Synlett, 1996, 761; (i) Ishikawa, T.; Tajima, Y.; Fukui, M.; Saito, S. Angew. Chem., Int. Ed. Engl., 1996, 35, 1863; (j) Goti, A.; Cardona, F. Brandi, A.; Picasso, S.; Vogel, P. Tetrahedron: Asymm., 1996, 7, 1659; (k) Hall, A.; Meldrum, K.P.; Therond, P.R.; Wightman, R.H. Synlett, 1997, 123; (l) Goti, A.; Cicchi, S.; Fedi, V.; Nannelli, L.; Brandi, A. J. Org. Chem., 1997, 62, 3119; (m) Closa, M.; de March, P.; Figueredo, M.; Font, J. Tetrahedron: Asymm., 1997, 8, 1031; (n) Goti, A.; Fedi, V.; Nannelli, L.; De Sarlo, F.; Brandi, A. Synlett, 1997, 577.
12. For the preparation and use in cycloadditions of enantiopure 1-pyrroline-N-oxides (five-ring cyclic nitrones) with (protected) hydroxy and hydroxy-methyl substituents, see: (a) Golik, J.; Wong, H.; Krishnan, B.; Vyas, D.M.; Doyle, T.W. Tetrahedron Lett., 1991, 32, 1851; (b) Ballini, R.; Marcantoni, E.; Petrini, M. J. Org. Chem., 1992, 57, 1316; (c) McCaig, A.E.; Wightman, R.H. Tetrahedron Lett., 1993, 34, 3939; (d) Cicchi, S.; Höld, I.; Brandi, A. J. Org. Chem., 1993, 58, 5274; (e) Cicchi, S.; Goti, A.; Brandi, A. J. Org. Chem., 1995, 60, 4743; (f) de March, P.; Figueredo, M.; Font, J.; Gallagher, T.; Milán, S. J. Chem. Soc., Chem. Commun., 1995, 2097; (g) Brandi, A.; Cicchi, S.; Cordera, F.M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem., 1995, 60, 6806; (h) Goti, A.; Cardona, F.; Brandi, A. Synlett, 1996, 761; (i) Ishikawa, T.; Tajima, Y.; Fukui, M.; Saito, S. Angew. Chem., Int. Ed. Engl., 1996, 35, 1863; (j) Goti, A.; Cardona, F. Brandi, A.; Picasso, S.; Vogel, P. Tetrahedron: Asymm., 1996, 7, 1659; (k) Hall, A.; Meldrum, K.P.; Therond, P.R.; Wightman, R.H. Synlett, 1997, 123; (l) Goti, A.; Cicchi, S.; Fedi, V.; Nannelli, L.; Brandi, A. J. Org. Chem., 1997, 62, 3119; (m) Closa, M.; de March, P.; Figueredo, M.; Font, J. Tetrahedron: Asymm., 1997, 8, 1031; (n) Goti, A.; Fedi, V.; Nannelli, L.; De Sarlo, F.; Brandi, A. Synlett, 1997, 577.
13. For the preparation and use in cycloadditions of enantiopure 1-pyrroline-N-oxides (five-ring cyclic nitrones) with (protected) hydroxy and hydroxy-methyl substituents, see: (a) Golik, J.; Wong, H.; Krishnan, B.; Vyas, D.M.; Doyle, T.W. Tetrahedron Lett., 1991, 32, 1851; (b) Ballini, R.; Marcantoni, E.; Petrini, M. J. Org. Chem., 1992, 57, 1316; (c) McCaig, A.E.; Wightman, R.H. Tetrahedron Lett., 1993, 34, 3939; (d) Cicchi, S.; Höld, I.; Brandi, A. J. Org. Chem., 1993, 58, 5274; (e) Cicchi, S.; Goti, A.; Brandi, A. J. Org. Chem., 1995, 60, 4743; (f) de March, P.; Figueredo, M.; Font, J.; Gallagher, T.; Milán, S. J. Chem. Soc., Chem. Commun., 1995, 2097; (g) Brandi, A.; Cicchi, S.; Cordera, F.M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem., 1995, 60, 6806; (h) Goti, A.; Cardona, F.; Brandi, A. Synlett, 1996, 761; (i) Ishikawa, T.; Tajima, Y.; Fukui, M.; Saito, S. Angew. Chem., Int. Ed. Engl., 1996, 35, 1863; (j) Goti, A.; Cardona, F. Brandi, A.; Picasso, S.; Vogel, P. Tetrahedron: Asymm., 1996, 7, 1659; (k) Hall, A.; Meldrum, K.P.; Therond, P.R.; Wightman, R.H. Synlett, 1997, 123; (l) Goti, A.; Cicchi, S.; Fedi, V.; Nannelli, L.; Brandi, A. J. Org. Chem., 1997, 62, 3119; (m) Closa, M.; de March, P.; Figueredo, M.; Font, J. Tetrahedron: Asymm., 1997, 8, 1031; (n) Goti, A.; Fedi, V.; Nannelli, L.; De Sarlo, F.; Brandi, A. Synlett, 1997, 577.
14. For the preparation and use in cycloadditions of enantiopure 1-pyrroline-N-oxides (five-ring cyclic nitrones) with (protected) hydroxy and hydroxy-methyl substituents, see: (a) Golik, J.; Wong, H.; Krishnan, B.; Vyas, D.M.; Doyle, T.W. Tetrahedron Lett., 1991, 32, 1851; (b) Ballini, R.; Marcantoni, E.; Petrini, M. J. Org. Chem., 1992, 57, 1316; (c) McCaig, A.E.; Wightman, R.H. Tetrahedron Lett., 1993, 34, 3939; (d) Cicchi, S.; Höld, I.; Brandi, A. J. Org. Chem., 1993, 58, 5274; (e) Cicchi, S.; Goti, A.; Brandi, A. J. Org. Chem., 1995, 60, 4743; (f) de March, P.; Figueredo, M.; Font, J.; Gallagher, T.; Milán, S. J. Chem. Soc., Chem. Commun., 1995, 2097; (g) Brandi, A.; Cicchi, S.; Cordera, F.M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem., 1995, 60, 6806; (h) Goti, A.; Cardona, F.; Brandi, A. Synlett, 1996, 761; (i) Ishikawa, T.; Tajima, Y.; Fukui, M.; Saito, S. Angew. Chem., Int. Ed. Engl., 1996, 35, 1863; (j) Goti, A.; Cardona, F. Brandi, A.; Picasso, S.; Vogel, P. Tetrahedron: Asymm., 1996, 7, 1659; (k) Hall, A.; Meldrum, K.P.; Therond, P.R.; Wightman, R.H. Synlett, 1997, 123; (l) Goti, A.; Cicchi, S.; Fedi, V.; Nannelli, L.; Brandi, A. J. Org. Chem., 1997, 62, 3119; (m) Closa, M.; de March, P.; Figueredo, M.; Font, J. Tetrahedron: Asymm., 1997, 8, 1031; (n) Goti, A.; Fedi, V.; Nannelli, L.; De Sarlo, F.; Brandi, A. Synlett, 1997, 577.
15. For the preparation and use in cycloadditions of enantiopure 1-pyrroline-N-oxides (five-ring cyclic nitrones) with (protected) hydroxy and hydroxy-methyl substituents, see: (a) Golik, J.; Wong, H.; Krishnan, B.; Vyas, D.M.; Doyle, T.W. Tetrahedron Lett., 1991, 32, 1851; (b) Ballini, R.; Marcantoni, E.; Petrini, M. J. Org. Chem., 1992, 57, 1316; (c) McCaig, A.E.; Wightman, R.H. Tetrahedron Lett., 1993, 34, 3939; (d) Cicchi, S.; Höld, I.; Brandi, A. J. Org. Chem., 1993, 58, 5274; (e) Cicchi, S.; Goti, A.; Brandi, A. J. Org. Chem., 1995, 60, 4743; (f) de March, P.; Figueredo, M.; Font, J.; Gallagher, T.; Milán, S. J. Chem. Soc., Chem. Commun., 1995, 2097; (g) Brandi, A.; Cicchi, S.; Cordera, F.M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem., 1995, 60, 6806; (h) Goti, A.; Cardona, F.; Brandi, A. Synlett, 1996, 761; (i) Ishikawa, T.; Tajima, Y.; Fukui, M.; Saito, S. Angew. Chem., Int. Ed. Engl., 1996, 35, 1863; (j) Goti, A.; Cardona, F. Brandi, A.; Picasso, S.; Vogel, P. Tetrahedron: Asymm., 1996, 7, 1659; (k) Hall, A.; Meldrum, K.P.; Therond, P.R.; Wightman, R.H. Synlett, 1997, 123; (l) Goti, A.; Cicchi, S.; Fedi, V.; Nannelli, L.; Brandi, A. J. Org. Chem., 1997, 62, 3119; (m) Closa, M.; de March, P.; Figueredo, M.; Font, J. Tetrahedron: Asymm., 1997, 8, 1031; (n) Goti, A.; Fedi, V.; Nannelli, L.; De Sarlo, F.; Brandi, A. Synlett, 1997, 577.
16. For the preparation and use in cycloadditions of enantiopure 1-pyrroline-N-oxides (five-ring cyclic nitrones) with (protected) hydroxy and hydroxy-methyl substituents, see: (a) Golik, J.; Wong, H.; Krishnan, B.; Vyas, D.M.; Doyle, T.W. Tetrahedron Lett., 1991, 32, 1851; (b) Ballini, R.; Marcantoni, E.; Petrini, M. J. Org. Chem., 1992, 57, 1316; (c) McCaig, A.E.; Wightman, R.H. Tetrahedron Lett., 1993, 34, 3939; (d) Cicchi, S.; Höld, I.; Brandi, A. J. Org. Chem., 1993, 58, 5274; (e) Cicchi, S.; Goti, A.; Brandi, A. J. Org. Chem., 1995, 60, 4743; (f) de March, P.; Figueredo, M.; Font, J.; Gallagher, T.; Milán, S. J. Chem. Soc., Chem. Commun., 1995, 2097; (g) Brandi, A.; Cicchi, S.; Cordera, F.M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem., 1995, 60, 6806; (h) Goti, A.; Cardona, F.; Brandi, A. Synlett, 1996, 761; (i) Ishikawa, T.; Tajima, Y.; Fukui, M.; Saito, S. Angew. Chem., Int. Ed. Engl., 1996, 35, 1863; (j) Goti, A.; Cardona, F. Brandi, A.; Picasso, S.; Vogel, P. Tetrahedron: Asymm., 1996, 7, 1659; (k) Hall, A.; Meldrum, K.P.; Therond, P.R.; Wightman, R.H. Synlett, 1997, 123; (l) Goti, A.; Cicchi, S.; Fedi, V.; Nannelli, L.; Brandi, A. J. Org. Chem., 1997, 62, 3119; (m) Closa, M.; de March, P.; Figueredo, M.; Font, J. Tetrahedron: Asymm., 1997, 8, 1031; (n) Goti, A.; Fedi, V.; Nannelli, L.; De Sarlo, F.; Brandi, A. Synlett, 1997, 577.
17. For the preparation and use in cycloadditions of enantiopure 1-pyrroline-N-oxides (five-ring cyclic nitrones) with (protected) hydroxy and hydroxy-methyl substituents, see: (a) Golik, J.; Wong, H.; Krishnan, B.; Vyas, D.M.; Doyle, T.W. Tetrahedron Lett., 1991, 32, 1851; (b) Ballini, R.; Marcantoni, E.; Petrini, M. J. Org. Chem., 1992, 57, 1316; (c) McCaig, A.E.; Wightman, R.H. Tetrahedron Lett., 1993, 34, 3939; (d) Cicchi, S.; Höld, I.; Brandi, A. J. Org. Chem., 1993, 58, 5274; (e) Cicchi, S.; Goti, A.; Brandi, A. J. Org. Chem., 1995, 60, 4743; (f) de March, P.; Figueredo, M.; Font, J.; Gallagher, T.; Milán, S. J. Chem. Soc., Chem. Commun., 1995, 2097; (g) Brandi, A.; Cicchi, S.; Cordera, F.M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem., 1995, 60, 6806; (h) Goti, A.; Cardona, F.; Brandi, A. Synlett, 1996, 761; (i) Ishikawa, T.; Tajima, Y.; Fukui, M.; Saito, S. Angew. Chem., Int. Ed. Engl., 1996, 35, 1863; (j) Goti, A.; Cardona, F. Brandi, A.; Picasso, S.; Vogel, P. Tetrahedron: Asymm., 1996, 7, 1659; (k) Hall, A.; Meldrum, K.P.; Therond, P.R.; Wightman, R.H. Synlett, 1997, 123; (l) Goti, A.; Cicchi, S.; Fedi, V.; Nannelli, L.; Brandi, A. J. Org. Chem., 1997, 62, 3119; (m) Closa, M.; de March, P.; Figueredo, M.; Font, J. Tetrahedron: Asymm., 1997, 8, 1031; (n) Goti, A.; Fedi, V.; Nannelli, L.; De Sarlo, F.; Brandi, A. Synlett, 1997, 577.
18. For the preparation and use in cycloadditions of enantiopure 1-pyrroline-N-oxides (five-ring cyclic nitrones) with (protected) hydroxy and hydroxy-methyl substituents, see: (a) Golik, J.; Wong, H.; Krishnan, B.; Vyas, D.M.; Doyle, T.W. Tetrahedron Lett., 1991, 32, 1851; (b) Ballini, R.; Marcantoni, E.; Petrini, M. J. Org. Chem., 1992, 57, 1316; (c) McCaig, A.E.; Wightman, R.H. Tetrahedron Lett., 1993, 34, 3939; (d) Cicchi, S.; Höld, I.; Brandi, A. J. Org. Chem., 1993, 58, 5274; (e) Cicchi, S.; Goti, A.; Brandi, A. J. Org. Chem., 1995, 60, 4743; (f) de March, P.; Figueredo, M.; Font, J.; Gallagher, T.; Milán, S. J. Chem. Soc., Chem. Commun., 1995, 2097; (g) Brandi, A.; Cicchi, S.; Cordera, F.M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem., 1995, 60, 6806; (h) Goti, A.; Cardona, F.; Brandi, A. Synlett, 1996, 761; (i) Ishikawa, T.; Tajima, Y.; Fukui, M.; Saito, S. Angew. Chem., Int. Ed. Engl., 1996, 35, 1863; (j) Goti, A.; Cardona, F. Brandi, A.; Picasso, S.; Vogel, P. Tetrahedron: Asymm., 1996, 7, 1659; (k) Hall, A.; Meldrum, K.P.; Therond, P.R.; Wightman, R.H. Synlett, 1997, 123; (l) Goti, A.; Cicchi, S.; Fedi, V.; Nannelli, L.; Brandi, A. J. Org. Chem., 1997, 62, 3119; (m) Closa, M.; de March, P.; Figueredo, M.; Font, J. Tetrahedron: Asymm., 1997, 8, 1031; (n) Goti, A.; Fedi, V.; Nannelli, L.; De Sarlo, F.; Brandi, A. Synlett, 1997, 577.
19. For the preparation and use in cycloadditions of enantiopure 1-pyrroline-N-oxides (five-ring cyclic nitrones) with (protected) hydroxy and hydroxy-methyl substituents, see: (a) Golik, J.; Wong, H.; Krishnan, B.; Vyas, D.M.; Doyle, T.W. Tetrahedron Lett., 1991, 32, 1851; (b) Ballini, R.; Marcantoni, E.; Petrini, M. J. Org. Chem., 1992, 57, 1316; (c) McCaig, A.E.; Wightman, R.H. Tetrahedron Lett., 1993, 34, 3939; (d) Cicchi, S.; Höld, I.; Brandi, A. J. Org. Chem., 1993, 58, 5274; (e) Cicchi, S.; Goti, A.; Brandi, A. J. Org. Chem., 1995, 60, 4743; (f) de March, P.; Figueredo, M.; Font, J.; Gallagher, T.; Milán, S. J. Chem. Soc., Chem. Commun., 1995, 2097; (g) Brandi, A.; Cicchi, S.; Cordera, F.M.; Frignoli, R.; Goti, A.; Picasso, S.; Vogel, P. J. Org. Chem., 1995, 60, 6806; (h) Goti, A.; Cardona, F.; Brandi, A. Synlett, 1996, 761; (i) Ishikawa, T.; Tajima, Y.; Fukui, M.; Saito, S. Angew. Chem., Int. Ed. Engl., 1996, 35, 1863; (j) Goti, A.; Cardona, F. Brandi, A.; Picasso, S.; Vogel, P. Tetrahedron: Asymm., 1996, 7, 1659; (k) Hall, A.; Meldrum, K.P.; Therond, P.R.; Wightman, R.H. Synlett, 1997, 123; (l) Goti, A.; Cicchi, S.; Fedi, V.; Nannelli, L.; Brandi, A. J. Org. Chem., 1997, 62, 3119; (m) Closa, M.; de March, P.; Figueredo, M.; Font, J. Tetrahedron: Asymm., 1997, 8, 1031; (n) Goti, A.; Fedi, V.; Nannelli, L.; De Sarlo, F.; Brandi, A. Synlett, 1997, 577.
20. e.g. Tufariello, J. J. Acc. Chem. Res. 1979, 12, 396; Tufariello, J. J.; Meckler, H.; Senaratne, H.P.A. Tetrahedron, 1985, 41, 3447.
21. e.g. Tufariello, J. J. Acc. Chem. Res. 1979, 12, 396; Tufariello, J. J.; Meckler, H.; Senaratne, H.P.A. Tetrahedron, 1985, 41, 3447.
22. Kiso, M.; Hasegawa, A. Carbohydr. Res., 1976, 52, 95.
23. Thompson, D.K.; Hubert, C.N.; Wightman, R.H. Tetrahedron, 1993, 49, 3827.
24. t.
25. For an alternative approach to the corresponding tosylate and its enantiomer using asymmetric epoxidation see: Häfele, B.; Schröter, D.; Jäger, V. Angew. Chem., Int. Ed. Engl., 1986, 25, 87.
26. Burdisso, M.; Gandolfi, R.; Grünanger, P.; Rastelli, A. J. Org. Chem., 1990, 55, 3427.