6-Deoxy-allo-nojirimycin in the racemic and D-series, 6-deoxy-D,L-talo-nojirimycin, their 1-deoxyderivatives and 6-deoxy-2-D,L-allosamine via hetero-Diels-Alder cycloadditions

Tetrahedron

Volumn 53, Issue 40, 1997, Pages 13769-13782

  Defoin, Albert ^a   Sarazin, Hervé ^a   Streich, Jacques ^a  

^a UNIVERSITÉ DE HAUTE ALSACE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOSUGAR;

ARTICLE; CARBOHYDRATE SYNTHESIS; CHIRALITY; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030930477     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00897-1     Document Type: Article

References (43)

1. Nojirimycin : Dondoni, A.; Merino, P.; Perrone, D., Tetrahedron 1993, 49, 2939 ; Anzeveno, P.B; Creemer, L. J., Tetrahedron Lett. 1990, 31, 2085 ; Chida, N.; Furuno, Y.; Ikemoto, H.; Ogawa, S., Carbohydr. Res. 1992, 257, 185 ; Stasik, B.; Beaupère, D.; Uzan, R.; Demailly, G.; Morin, Ch., Compt. Rend. Acad. Sci. Paris 1990, 311, Sér.II, 521 ; Tsuda, Y.; Okuno, Y.; Kanemitsu, K., Heterocycles 1988, 27, 63. Manno-nojirimycin : Legler, G.; Jülich, E.; Carbohydr. Res. 1984, 128, 61. Galactostatine : Chida, N.; Tanikawa, T.; Tobe, T.; Ogawa, S., J. Chem. Soc., Chem. Commun. 1994, 1247 ; Dondoni, A.; Merino, P.; Perrone, D., J. Chem. Soc., Chem. Commun. 1991, 1576 ; Aoyagi, S.; Fujimaki, S.; Yamazaki, N.; Kibayashi, Ch., J. Org. Chem. 1991, 56, 815 ; Heterocycles 1990, 30, 783. Legler, G.; Pohl, St., Carbohydr. Res. 1986, 55, 119. 1-Deoxy-nojirimycin (review) : Hughes, A.B.; Rudge, A.J., Nat. Prod. Rep. 1994, 135.
2. Nojirimycin : Dondoni, A.; Merino, P.; Perrone, D., Tetrahedron 1993, 49, 2939 ; Anzeveno, P.B; Creemer, L. J., Tetrahedron Lett. 1990, 31, 2085 ; Chida, N.; Furuno, Y.; Ikemoto, H.; Ogawa, S., Carbohydr. Res. 1992, 257, 185 ; Stasik, B.; Beaupère, D.; Uzan, R.; Demailly, G.; Morin, Ch., Compt. Rend. Acad. Sci. Paris 1990, 311, Sér.II, 521 ; Tsuda, Y.; Okuno, Y.; Kanemitsu, K., Heterocycles 1988, 27, 63. Manno-nojirimycin : Legler, G.; Jülich, E.; Carbohydr. Res. 1984, 128, 61. Galactostatine : Chida, N.; Tanikawa, T.; Tobe, T.; Ogawa, S., J. Chem. Soc., Chem. Commun. 1994, 1247 ; Dondoni, A.; Merino, P.; Perrone, D., J. Chem. Soc., Chem. Commun. 1991, 1576 ; Aoyagi, S.; Fujimaki, S.; Yamazaki, N.; Kibayashi, Ch., J. Org. Chem. 1991, 56, 815 ; Heterocycles 1990, 30, 783. Legler, G.; Pohl, St., Carbohydr. Res. 1986, 55, 119. 1-Deoxy-nojirimycin (review) : Hughes, A.B.; Rudge, A.J., Nat. Prod. Rep. 1994, 135.
3. Nojirimycin : Dondoni, A.; Merino, P.; Perrone, D., Tetrahedron 1993, 49, 2939 ; Anzeveno, P.B; Creemer, L. J., Tetrahedron Lett. 1990, 31, 2085 ; Chida, N.; Furuno, Y.; Ikemoto, H.; Ogawa, S., Carbohydr. Res. 1992, 257, 185 ; Stasik, B.; Beaupère, D.; Uzan, R.; Demailly, G.; Morin, Ch., Compt. Rend. Acad. Sci. Paris 1990, 311, Sér.II, 521 ; Tsuda, Y.; Okuno, Y.; Kanemitsu, K., Heterocycles 1988, 27, 63. Manno-nojirimycin : Legler, G.; Jülich, E.; Carbohydr. Res. 1984, 128, 61. Galactostatine : Chida, N.; Tanikawa, T.; Tobe, T.; Ogawa, S., J. Chem. Soc., Chem. Commun. 1994, 1247 ; Dondoni, A.; Merino, P.; Perrone, D., J. Chem. Soc., Chem. Commun. 1991, 1576 ; Aoyagi, S.; Fujimaki, S.; Yamazaki, N.; Kibayashi, Ch., J. Org. Chem. 1991, 56, 815 ; Heterocycles 1990, 30, 783. Legler, G.; Pohl, St., Carbohydr. Res. 1986, 55, 119. 1-Deoxy-nojirimycin (review) : Hughes, A.B.; Rudge, A.J., Nat. Prod. Rep. 1994, 135.
4. Nojirimycin : Dondoni, A.; Merino, P.; Perrone, D., Tetrahedron 1993, 49, 2939 ; Anzeveno, P.B; Creemer, L. J., Tetrahedron Lett. 1990, 31, 2085 ; Chida, N.; Furuno, Y.; Ikemoto, H.; Ogawa, S., Carbohydr. Res. 1992, 257, 185 ; Stasik, B.; Beaupère, D.; Uzan, R.; Demailly, G.; Morin, Ch., Compt. Rend. Acad. Sci. Paris 1990, 311, Sér.II, 521 ; Tsuda, Y.; Okuno, Y.; Kanemitsu, K., Heterocycles 1988, 27, 63. Manno-nojirimycin : Legler, G.; Jülich, E.; Carbohydr. Res. 1984, 128, 61. Galactostatine : Chida, N.; Tanikawa, T.; Tobe, T.; Ogawa, S., J. Chem. Soc., Chem. Commun. 1994, 1247 ; Dondoni, A.; Merino, P.; Perrone, D., J. Chem. Soc., Chem. Commun. 1991, 1576 ; Aoyagi, S.; Fujimaki, S.; Yamazaki, N.; Kibayashi, Ch., J. Org. Chem. 1991, 56, 815 ; Heterocycles 1990, 30, 783. Legler, G.; Pohl, St., Carbohydr. Res. 1986, 55, 119. 1-Deoxy-nojirimycin (review) : Hughes, A.B.; Rudge, A.J., Nat. Prod. Rep. 1994, 135.
5. Nojirimycin : Dondoni, A.; Merino, P.; Perrone, D., Tetrahedron 1993, 49, 2939 ; Anzeveno, P.B; Creemer, L. J., Tetrahedron Lett. 1990, 31, 2085 ; Chida, N.; Furuno, Y.; Ikemoto, H.; Ogawa, S., Carbohydr. Res. 1992, 257, 185 ; Stasik, B.; Beaupère, D.; Uzan, R.; Demailly, G.; Morin, Ch., Compt. Rend. Acad. Sci. Paris 1990, 311, Sér.II, 521 ; Tsuda, Y.; Okuno, Y.; Kanemitsu, K., Heterocycles 1988, 27, 63. Manno-nojirimycin : Legler, G.; Jülich, E.; Carbohydr. Res. 1984, 128, 61. Galactostatine : Chida, N.; Tanikawa, T.; Tobe, T.; Ogawa, S., J. Chem. Soc., Chem. Commun. 1994, 1247 ; Dondoni, A.; Merino, P.; Perrone, D., J. Chem. Soc., Chem. Commun. 1991, 1576 ; Aoyagi, S.; Fujimaki, S.; Yamazaki, N.; Kibayashi, Ch., J. Org. Chem. 1991, 56, 815 ; Heterocycles 1990, 30, 783. Legler, G.; Pohl, St., Carbohydr. Res. 1986, 55, 119. 1-Deoxy-nojirimycin (review) : Hughes, A.B.; Rudge, A.J., Nat. Prod. Rep. 1994, 135.
6. Nojirimycin : Dondoni, A.; Merino, P.; Perrone, D., Tetrahedron 1993, 49, 2939 ; Anzeveno, P.B; Creemer, L. J., Tetrahedron Lett. 1990, 31, 2085 ; Chida, N.; Furuno, Y.; Ikemoto, H.; Ogawa, S., Carbohydr. Res. 1992, 257, 185 ; Stasik, B.; Beaupère, D.; Uzan, R.; Demailly, G.; Morin, Ch., Compt. Rend. Acad. Sci. Paris 1990, 311, Sér.II, 521 ; Tsuda, Y.; Okuno, Y.; Kanemitsu, K., Heterocycles 1988, 27, 63. Manno-nojirimycin : Legler, G.; Jülich, E.; Carbohydr. Res. 1984, 128, 61. Galactostatine : Chida, N.; Tanikawa, T.; Tobe, T.; Ogawa, S., J. Chem. Soc., Chem. Commun. 1994, 1247 ; Dondoni, A.; Merino, P.; Perrone, D., J. Chem. Soc., Chem. Commun. 1991, 1576 ; Aoyagi, S.; Fujimaki, S.; Yamazaki, N.; Kibayashi, Ch., J. Org. Chem. 1991, 56, 815 ; Heterocycles 1990, 30, 783. Legler, G.; Pohl, St., Carbohydr. Res. 1986, 55, 119. 1-Deoxy-nojirimycin (review) : Hughes, A.B.; Rudge, A.J., Nat. Prod. Rep. 1994, 135.
7. Nojirimycin : Dondoni, A.; Merino, P.; Perrone, D., Tetrahedron 1993, 49, 2939 ; Anzeveno, P.B; Creemer, L. J., Tetrahedron Lett. 1990, 31, 2085 ; Chida, N.; Furuno, Y.; Ikemoto, H.; Ogawa, S., Carbohydr. Res. 1992, 257, 185 ; Stasik, B.; Beaupère, D.; Uzan, R.; Demailly, G.; Morin, Ch., Compt. Rend. Acad. Sci. Paris 1990, 311, Sér.II, 521 ; Tsuda, Y.; Okuno, Y.; Kanemitsu, K., Heterocycles 1988, 27, 63. Manno-nojirimycin : Legler, G.; Jülich, E.; Carbohydr. Res. 1984, 128, 61. Galactostatine : Chida, N.; Tanikawa, T.; Tobe, T.; Ogawa, S., J. Chem. Soc., Chem. Commun. 1994, 1247 ; Dondoni, A.; Merino, P.; Perrone, D., J. Chem. Soc., Chem. Commun. 1991, 1576 ; Aoyagi, S.; Fujimaki, S.; Yamazaki, N.; Kibayashi, Ch., J. Org. Chem. 1991, 56, 815 ; Heterocycles 1990, 30, 783. Legler, G.; Pohl, St., Carbohydr. Res. 1986, 55, 119. 1-Deoxy-nojirimycin (review) : Hughes, A.B.; Rudge, A.J., Nat. Prod. Rep. 1994, 135.
8. Nojirimycin : Dondoni, A.; Merino, P.; Perrone, D., Tetrahedron 1993, 49, 2939 ; Anzeveno, P.B; Creemer, L. J., Tetrahedron Lett. 1990, 31, 2085 ; Chida, N.; Furuno, Y.; Ikemoto, H.; Ogawa, S., Carbohydr. Res. 1992, 257, 185 ; Stasik, B.; Beaupère, D.; Uzan, R.; Demailly, G.; Morin, Ch., Compt. Rend. Acad. Sci. Paris 1990, 311, Sér.II, 521 ; Tsuda, Y.; Okuno, Y.; Kanemitsu, K., Heterocycles 1988, 27, 63. Manno-nojirimycin : Legler, G.; Jülich, E.; Carbohydr. Res. 1984, 128, 61. Galactostatine : Chida, N.; Tanikawa, T.; Tobe, T.; Ogawa, S., J. Chem. Soc., Chem. Commun. 1994, 1247 ; Dondoni, A.; Merino, P.; Perrone, D., J. Chem. Soc., Chem. Commun. 1991, 1576 ; Aoyagi, S.; Fujimaki, S.; Yamazaki, N.; Kibayashi, Ch., J. Org. Chem. 1991, 56, 815 ; Heterocycles 1990, 30, 783. Legler, G.; Pohl, St., Carbohydr. Res. 1986, 55, 119. 1-Deoxy-nojirimycin (review) : Hughes, A.B.; Rudge, A.J., Nat. Prod. Rep. 1994, 135.
9. Nojirimycin : Dondoni, A.; Merino, P.; Perrone, D., Tetrahedron 1993, 49, 2939 ; Anzeveno, P.B; Creemer, L. J., Tetrahedron Lett. 1990, 31, 2085 ; Chida, N.; Furuno, Y.; Ikemoto, H.; Ogawa, S., Carbohydr. Res. 1992, 257, 185 ; Stasik, B.; Beaupère, D.; Uzan, R.; Demailly, G.; Morin, Ch., Compt. Rend. Acad. Sci. Paris 1990, 311, Sér.II, 521 ; Tsuda, Y.; Okuno, Y.; Kanemitsu, K., Heterocycles 1988, 27, 63. Manno-nojirimycin : Legler, G.; Jülich, E.; Carbohydr. Res. 1984, 128, 61. Galactostatine : Chida, N.; Tanikawa, T.; Tobe, T.; Ogawa, S., J. Chem. Soc., Chem. Commun. 1994, 1247 ; Dondoni, A.; Merino, P.; Perrone, D., J. Chem. Soc., Chem. Commun. 1991, 1576 ; Aoyagi, S.; Fujimaki, S.; Yamazaki, N.; Kibayashi, Ch., J. Org. Chem. 1991, 56, 815 ; Heterocycles 1990, 30, 783. Legler, G.; Pohl, St., Carbohydr. Res. 1986, 55, 119. 1-Deoxy-nojirimycin (review) : Hughes, A.B.; Rudge, A.J., Nat. Prod. Rep. 1994, 135.
10. Nojirimycin : Dondoni, A.; Merino, P.; Perrone, D., Tetrahedron 1993, 49, 2939 ; Anzeveno, P.B; Creemer, L. J., Tetrahedron Lett. 1990, 31, 2085 ; Chida, N.; Furuno, Y.; Ikemoto, H.; Ogawa, S., Carbohydr. Res. 1992, 257, 185 ; Stasik, B.; Beaupère, D.; Uzan, R.; Demailly, G.; Morin, Ch., Compt. Rend. Acad. Sci. Paris 1990, 311, Sér.II, 521 ; Tsuda, Y.; Okuno, Y.; Kanemitsu, K., Heterocycles 1988, 27, 63. Manno-nojirimycin : Legler, G.; Jülich, E.; Carbohydr. Res. 1984, 128, 61. Galactostatine : Chida, N.; Tanikawa, T.; Tobe, T.; Ogawa, S., J. Chem. Soc., Chem. Commun. 1994, 1247 ; Dondoni, A.; Merino, P.; Perrone, D., J. Chem. Soc., Chem. Commun. 1991, 1576 ; Aoyagi, S.; Fujimaki, S.; Yamazaki, N.; Kibayashi, Ch., J. Org. Chem. 1991, 56, 815 ; Heterocycles 1990, 30, 783. Legler, G.; Pohl, St., Carbohydr. Res. 1986, 55, 119. 1-Deoxy-nojirimycin (review) : Hughes, A.B.; Rudge, A.J., Nat. Prod. Rep. 1994, 135.
11. Nojirimycin : Dondoni, A.; Merino, P.; Perrone, D., Tetrahedron 1993, 49, 2939 ; Anzeveno, P.B; Creemer, L. J., Tetrahedron Lett. 1990, 31, 2085 ; Chida, N.; Furuno, Y.; Ikemoto, H.; Ogawa, S., Carbohydr. Res. 1992, 257, 185 ; Stasik, B.; Beaupère, D.; Uzan, R.; Demailly, G.; Morin, Ch., Compt. Rend. Acad. Sci. Paris 1990, 311, Sér.II, 521 ; Tsuda, Y.; Okuno, Y.; Kanemitsu, K., Heterocycles 1988, 27, 63. Manno-nojirimycin : Legler, G.; Jülich, E.; Carbohydr. Res. 1984, 128, 61. Galactostatine : Chida, N.; Tanikawa, T.; Tobe, T.; Ogawa, S., J. Chem. Soc., Chem. Commun. 1994, 1247 ; Dondoni, A.; Merino, P.; Perrone, D., J. Chem. Soc., Chem. Commun. 1991, 1576 ; Aoyagi, S.; Fujimaki, S.; Yamazaki, N.; Kibayashi, Ch., J. Org. Chem. 1991, 56, 815 ; Heterocycles 1990, 30, 783. Legler, G.; Pohl, St., Carbohydr. Res. 1986, 55, 119. 1-Deoxy-nojirimycin (review) : Hughes, A.B.; Rudge, A.J., Nat. Prod. Rep. 1994, 135.
12. Nojirimycin : Dondoni, A.; Merino, P.; Perrone, D., Tetrahedron 1993, 49, 2939 ; Anzeveno, P.B; Creemer, L. J., Tetrahedron Lett. 1990, 31, 2085 ; Chida, N.; Furuno, Y.; Ikemoto, H.; Ogawa, S., Carbohydr. Res. 1992, 257, 185 ; Stasik, B.; Beaupère, D.; Uzan, R.; Demailly, G.; Morin, Ch., Compt. Rend. Acad. Sci. Paris 1990, 311, Sér.II, 521 ; Tsuda, Y.; Okuno, Y.; Kanemitsu, K., Heterocycles 1988, 27, 63. Manno-nojirimycin : Legler, G.; Jülich, E.; Carbohydr. Res. 1984, 128, 61. Galactostatine : Chida, N.; Tanikawa, T.; Tobe, T.; Ogawa, S., J. Chem. Soc., Chem. Commun. 1994, 1247 ; Dondoni, A.; Merino, P.; Perrone, D., J. Chem. Soc., Chem. Commun. 1991, 1576 ; Aoyagi, S.; Fujimaki, S.; Yamazaki, N.; Kibayashi, Ch., J. Org. Chem. 1991, 56, 815 ; Heterocycles 1990, 30, 783. Legler, G.; Pohl, St., Carbohydr. Res. 1986, 55, 119. 1-Deoxy-nojirimycin (review) : Hughes, A.B.; Rudge, A.J., Nat. Prod. Rep. 1994, 135.
13. Wong, Ch.-H.; Halcomb, R.L.; Ichikawa, Y.; Kajimoto, T., Angew. Chem. Int. Ed. 1995, 34, 412 ; 521.
14. Vasella, A.; Voeffray, R., Helv. Chim. Acta 1982, 65, 1134 ; Wagner, J.; Vogel, P., Tetrahedron Lett. 1991, 52, 3169.
15. Vasella, A.; Voeffray, R., Helv. Chim. Acta 1982, 65, 1134 ; Wagner, J.; Vogel, P., Tetrahedron Lett. 1991, 52, 3169.
16. Auberson, Y.; Vogel, P., Angew. Chem. Int. Ed. 1989, 28, 1498.
17. Defoin, A.; Fritz, H.; Schmidlin, Ch.; Streith, J., Helv. Chim. Acta 1987, 70, 554
18. Defoin, A.; Fritz, H.; Geffroy, G.; Streith, J., Helv. Chim. Acta 1988, 71, 1642.
19. a) Defoin, A.; Sarazin, H.; Streith, J., Tetrahedron Lett. 1993, 34, 4327.
20. b) Defoin, A.; Sarazin, H.; Streith, J., Synlett. 1995, 1187
21. Hussain, A.; Wyatt, P.B., Tetrahedron 1993, 49, 2123.
22. Defoin, A.; Sarazin, H.; Streith, J., Helv. Chim. Acta 1996, 79, 560.
23. Oppolzer, W.; Barras, J.-P., Helv. Chim. Acta 1987, 70, 1666.
24. Felber, H.; Kresze, G.; Prewo, R.; Vasella, A., Helv. Chim. Acta 1986, 69, 1137 ; corrigendum : Braun, H.; Charles, R.; Kresze, G.; Sabuni, M.; Winkler, J., Liebigs Ann. Chem. 1987, 1129 ; Braun, H.; Felber, H.; Kresze, G.; Schmidtchen, Fr.P.; Prewo, R.; Vasella, A., Liebigs Ann. Chem. 1993, 261.
25. Felber, H.; Kresze, G.; Prewo, R.; Vasella, A., Helv. Chim. Acta 1986, 69, 1137 ; corrigendum : Braun, H.; Charles, R.; Kresze, G.; Sabuni, M.; Winkler, J., Liebigs Ann. Chem. 1987, 1129 ; Braun, H.; Felber, H.; Kresze, G.; Schmidtchen, Fr.P.; Prewo, R.; Vasella, A., Liebigs Ann. Chem. 1993, 261.
26. Felber, H.; Kresze, G.; Prewo, R.; Vasella, A., Helv. Chim. Acta 1986, 69, 1137 ; corrigendum : Braun, H.; Charles, R.; Kresze, G.; Sabuni, M.; Winkler, J., Liebigs Ann. Chem. 1987, 1129 ; Braun, H.; Felber, H.; Kresze, G.; Schmidtchen, Fr.P.; Prewo, R.; Vasella, A., Liebigs Ann. Chem. 1993, 261.
27. 3/MeOH), i.e. a immediate deprotection into sorbaldehyde. We have tried to use other chiral nitroso dienophiles derived from mandelic acid or from pyrrolidines (Defoin, A.; Brouillard-Poichet, A.; Streith, J. Helv. Chim. Acta 1992, 75, 109) without any reaction occurring, most probably because the diene 3 was not reactive enough. No attempts have been made to use the chiral auxiliaries derived from camphor (Gouverneur, V.; Dive, G.; Ghosez, A. Tetrahedron : Asymmetry 1991, 2, 1173 ; Martin, St.,F.; Hartmann, M.; Josey, J.A. Tetrahedron Lett. 1992, 33, 3583.
28. 3/MeOH), i.e. a immediate deprotection into sorbaldehyde. We have tried to use other chiral nitroso dienophiles derived from mandelic acid or from pyrrolidines (Defoin, A.; Brouillard-Poichet, A.; Streith, J. Helv. Chim. Acta 1992, 75, 109) without any reaction occurring, most probably because the diene 3 was not reactive enough. No attempts have been made to use the chiral auxiliaries derived from camphor (Gouverneur, V.; Dive, G.; Ghosez, A. Tetrahedron : Asymmetry 1991, 2, 1173 ; Martin, St.,F.; Hartmann, M.; Josey, J.A. Tetrahedron Lett. 1992, 33, 3583.
29. 3/MeOH), i.e. a immediate deprotection into sorbaldehyde. We have tried to use other chiral nitroso dienophiles derived from mandelic acid or from pyrrolidines (Defoin, A.; Brouillard-Poichet, A.; Streith, J. Helv. Chim. Acta 1992, 75, 109) without any reaction occurring, most probably because the diene 3 was not reactive enough. No attempts have been made to use the chiral auxiliaries derived from camphor (Gouverneur, V.; Dive, G.; Ghosez, A. Tetrahedron : Asymmetry 1991, 2, 1173 ; Martin, St.,F.; Hartmann, M.; Josey, J.A. Tetrahedron Lett. 1992, 33, 3583.
30. 3/MeOH), i.e. a immediate deprotection into sorbaldehyde. We have tried to use other chiral nitroso dienophiles derived from mandelic acid or from pyrrolidines (Defoin, A.; Brouillard-Poichet, A.; Streith, J. Helv. Chim. Acta 1992, 75, 109) without any reaction occurring, most probably because the diene 3 was not reactive enough. No attempts have been made to use the chiral auxiliaries derived from camphor (Gouverneur, V.; Dive, G.; Ghosez, A. Tetrahedron : Asymmetry 1991, 2, 1173 ; Martin, St.,F.; Hartmann, M.; Josey, J.A. Tetrahedron Lett. 1992, 33, 3583.
31. Paulsen, H.; Leupold, F.; Todt, Kl., Liebigs Ann. Chem. 1966, 692, 200 ; Paulsen, H.; Steinert, K.; Heyns, K., Chem. Ber. 1970, 103, 1599 ; Paulsen, H.; Propp, K.; Brüning, J., Chem. Ber. 1969, 102, 469 ; Ingles, D.L, Tetrahedron Lett. 1965, 1317.
32. Paulsen, H.; Leupold, F.; Todt, Kl., Liebigs Ann. Chem. 1966, 692, 200 ; Paulsen, H.; Steinert, K.; Heyns, K., Chem. Ber. 1970, 103, 1599 ; Paulsen, H.; Propp, K.; Brüning, J., Chem. Ber. 1969, 102, 469 ; Ingles, D.L, Tetrahedron Lett. 1965, 1317.
33. Paulsen, H.; Leupold, F.; Todt, Kl., Liebigs Ann. Chem. 1966, 692, 200 ; Paulsen, H.; Steinert, K.; Heyns, K., Chem. Ber. 1970, 103, 1599 ; Paulsen, H.; Propp, K.; Brüning, J., Chem. Ber. 1969, 102, 469 ; Ingles, D.L, Tetrahedron Lett. 1965, 1317.
34. Paulsen, H.; Leupold, F.; Todt, Kl., Liebigs Ann. Chem. 1966, 692, 200 ; Paulsen, H.; Steinert, K.; Heyns, K., Chem. Ber. 1970, 103, 1599 ; Paulsen, H.; Propp, K.; Brüning, J., Chem. Ber. 1969, 102, 469 ; Ingles, D.L, Tetrahedron Lett. 1965, 1317.
35. Horton, D. ; Wander, J.D., in The Carbohydrates, Chemistry and Biochemistry ; Pigman, W.; Horton, D., Eds., Academic Press, New York, 1980, Vol 1B, p 726.
36. Brendel, Kl.; Gross, P.H.; Zimmermann Jr., H.K., Liebigs Ann. Chem. 1966, 691, 192 ; Horton, D.; Liav, A., Carbohydr. Res. 1976, 47, 326.
37. Brendel, Kl.; Gross, P.H.; Zimmermann Jr., H.K., Liebigs Ann. Chem. 1966, 691, 192 ; Horton, D.; Liav, A., Carbohydr. Res. 1976, 47, 326.
38. Perry, M.B.; Daoust, V., Carbohydr. Res. 1973, 31, 131.
39. Jäger, V.; Schröter, D., Synthesis 1990, 556.
40. Paulsen, H.; Todt, Kl., Chem. Ber. 1967, 100, 3385.
41. Stevens, J.D.; Fletcher Jr, H.G., J. Org. Chem. 1968, 33, 1799.
42. Akashi, K.; Palermo, R.E.; Sharpless, K.B., J. Org. Chem. 1978, 43, 2063.
43. Paulsen, H.; Koebernick, H.; Schönherr, H., Chem. Ber. 1972, 105, 1515.