Synthesis of α- and β-D-(1→6)-C-Disaccharides by Wittig Olefination of Formyl C-Glycosides with Glycopyranose 6-Phosphoranes

Journal of Organic Chemistry

Volumn 62, Issue 23, 1997, Pages 8114-8124

  Dondoni, Alessandro ^a   Zuurmond, Helene M ^a   Boscarato, Alessia ^a  

^a UNIVERSITY OF FERRARA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001346586     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971177n     Document Type: Article

References (98)

1. (a) Modern Methods in Carbohydrate Synthesis; Khan, S. H., O'Neill, R. A., Eds.; Harwood Academic Publishers: Amsterdam, 1996.
2. (b) Preparative Carbohydrate Chemistry; Hanessian, S., Ed.; Marcel Dekker, Inc.: New York, 1997.
3. 2: Boger, D. L.; Honda, T. J. Am. Chem. Soc. 1994, 116, 5647. (c) Anthracycline disaccharides: Animati, F.; Arcamone, F.; Berettoni, M.; Cipollone, A.; Franciotto, M.; Lombardi, P. J. Chem. Soc., Perkin Trans. 1 1996, 1327. (d) Palytoxin: Armstrong, R. W.; Beau, J.-M.; Cheon, S. H.; Christ, W. J.; Fujioka, H.; Ham, W.-H.; Hawkins, L. D.; Jin, H.; Kang, S. H.; Kishi, Y.; Martinelli, M. J.; McWorter, W. W., Jr.; Mizuno, M.; Nakata, M; Stutz, A. E.; Talamas, F. X.; Taniguchi, M.; Tino, J. A.; Ueda, J. I.; White, J. B.; Yonaga, M. J. Am. Chem. Soc. 1989, 111, 7525 and references therein. (e) Vancomycin and analogues: Rama Rao, A. V.; Gurjar, M. K.; Reddy, L.; Rao, A. S. Chem. Rev. (Washington, D.C.) 1995, 95, 2135.
4. 2: Boger, D. L.; Honda, T. J. Am. Chem. Soc. 1994, 116, 5647. (c) Anthracycline disaccharides: Animati, F.; Arcamone, F.; Berettoni, M.; Cipollone, A.; Franciotto, M.; Lombardi, P. J. Chem. Soc., Perkin Trans. 1 1996, 1327. (d) Palytoxin: Armstrong, R. W.; Beau, J.-M.; Cheon, S. H.; Christ, W. J.; Fujioka, H.; Ham, W.-H.; Hawkins, L. D.; Jin, H.; Kang, S. H.; Kishi, Y.; Martinelli, M. J.; McWorter, W. W., Jr.; Mizuno, M.; Nakata, M; Stutz, A. E.; Talamas, F. X.; Taniguchi, M.; Tino, J. A.; Ueda, J. I.; White, J. B.; Yonaga, M. J. Am. Chem. Soc. 1989, 111, 7525 and references therein. (e) Vancomycin and analogues: Rama Rao, A. V.; Gurjar, M. K.; Reddy, L.; Rao, A. S. Chem. Rev. (Washington, D.C.) 1995, 95, 2135.
5. 2: Boger, D. L.; Honda, T. J. Am. Chem. Soc. 1994, 116, 5647. (c) Anthracycline disaccharides: Animati, F.; Arcamone, F.; Berettoni, M.; Cipollone, A.; Franciotto, M.; Lombardi, P. J. Chem. Soc., Perkin Trans. 1 1996, 1327. (d) Palytoxin: Armstrong, R. W.; Beau, J.-M.; Cheon, S. H.; Christ, W. J.; Fujioka, H.; Ham, W.-H.; Hawkins, L. D.; Jin, H.; Kang, S. H.; Kishi, Y.; Martinelli, M. J.; McWorter, W. W., Jr.; Mizuno, M.; Nakata, M; Stutz, A. E.; Talamas, F. X.; Taniguchi, M.; Tino, J. A.; Ueda, J. I.; White, J. B.; Yonaga, M. J. Am. Chem. Soc. 1989, 111, 7525 and references therein. (e) Vancomycin and analogues: Rama Rao, A. V.; Gurjar, M. K.; Reddy, L.; Rao, A. S. Chem. Rev. (Washington, D.C.) 1995, 95, 2135.
6. 2: Boger, D. L.; Honda, T. J. Am. Chem. Soc. 1994, 116, 5647. (c) Anthracycline disaccharides: Animati, F.; Arcamone, F.; Berettoni, M.; Cipollone, A.; Franciotto, M.; Lombardi, P. J. Chem. Soc., Perkin Trans. 1 1996, 1327. (d) Palytoxin: Armstrong, R. W.; Beau, J.-M.; Cheon, S. H.; Christ, W. J.; Fujioka, H.; Ham, W.-H.; Hawkins, L. D.; Jin, H.; Kang, S. H.; Kishi, Y.; Martinelli, M. J.; McWorter, W. W., Jr.; Mizuno, M.; Nakata, M; Stutz, A. E.; Talamas, F. X.; Taniguchi, M.; Tino, J. A.; Ueda, J. I.; White, J. B.; Yonaga, M. J. Am. Chem. Soc. 1989, 111, 7525 and references therein. (e) Vancomycin and analogues: Rama Rao, A. V.; Gurjar, M. K.; Reddy, L.; Rao, A. S. Chem. Rev. (Washington, D.C.) 1995, 95, 2135.
7. 2: Boger, D. L.; Honda, T. J. Am. Chem. Soc. 1994, 116, 5647. (c) Anthracycline disaccharides: Animati, F.; Arcamone, F.; Berettoni, M.; Cipollone, A.; Franciotto, M.; Lombardi, P. J. Chem. Soc., Perkin Trans. 1 1996, 1327. (d) Palytoxin: Armstrong, R. W.; Beau, J.-M.; Cheon, S. H.; Christ, W. J.; Fujioka, H.; Ham, W.-H.; Hawkins, L. D.; Jin, H.; Kang, S. H.; Kishi, Y.; Martinelli, M. J.; McWorter, W. W., Jr.; Mizuno, M.; Nakata, M; Stutz, A. E.; Talamas, F. X.; Taniguchi, M.; Tino, J. A.; Ueda, J. I.; White, J. B.; Yonaga, M. J. Am. Chem. Soc. 1989, 111, 7525 and references therein. (e) Vancomycin and analogues: Rama Rao, A. V.; Gurjar, M. K.; Reddy, L.; Rao, A. S. Chem. Rev. (Washington, D.C.) 1995, 95, 2135.
8. (a) For reviews on classical and improved methods, see: Paulsen, H. Angew. Chem., Int. Ed. Engl. 1982, 21, 155. Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1986, 25, 212. Toshima, T.; Tatsuta, K. Chem. Rev. (Washington, D.C.) 1993, 93, 1503. Boons, G. J. Tetrahedron 1996, 52, 1095. Boons, G. J. Contemp. Org. Synth. 1996, 3, 173.
9. (a) For reviews on classical and improved methods, see: Paulsen, H. Angew. Chem., Int. Ed. Engl. 1982, 21, 155. Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1986, 25, 212. Toshima, T.; Tatsuta, K. Chem. Rev. (Washington, D.C.) 1993, 93, 1503. Boons, G. J. Tetrahedron 1996, 52, 1095. Boons, G. J. Contemp. Org. Synth. 1996, 3, 173.
10. (a) For reviews on classical and improved methods, see: Paulsen, H. Angew. Chem., Int. Ed. Engl. 1982, 21, 155. Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1986, 25, 212. Toshima, T.; Tatsuta, K. Chem. Rev. (Washington, D.C.) 1993, 93, 1503. Boons, G. J. Tetrahedron 1996, 52, 1095. Boons, G. J. Contemp. Org. Synth. 1996, 3, 173.
11. (a) For reviews on classical and improved methods, see: Paulsen, H. Angew. Chem., Int. Ed. Engl. 1982, 21, 155. Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1986, 25, 212. Toshima, T.; Tatsuta, K. Chem. Rev. (Washington, D.C.) 1993, 93, 1503. Boons, G. J. Tetrahedron 1996, 52, 1095. Boons, G. J. Contemp. Org. Synth. 1996, 3, 173.
12. (a) For reviews on classical and improved methods, see: Paulsen, H. Angew. Chem., Int. Ed. Engl. 1982, 21, 155. Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1986, 25, 212. Toshima, T.; Tatsuta, K. Chem. Rev. (Washington, D.C.) 1993, 93, 1503. Boons, G. J. Tetrahedron 1996, 52, 1095. Boons, G. J. Contemp. Org. Synth. 1996, 3, 173.
13. (b) For innovative methods, see: Boger, D. L.; Honda, T. J. Am. Chem. Soc. 1994, 116, 5647. Kondo, H.; Aoki, S.; Ichikawa, Y.; Halcomb, R. L.; Ritzen, H.; Wong, C.-H. J. Org. Chem. 1994, 59, 864. Nuller, T.; Schneider, R.; Schmidt, R. R. Tetrahedron Lett. 1994, 35, 4763. Watanabe, Y.; Nakamoto, C.; Yammamoto, S.; Ozaki, S. Tetrahedron 1994, 50, 6523. Yamanoi, T.; Nakamura, K.; Takeyama, H.; Yanagihara, Y. Bull. Chem. Soc. Jpn 1994, 67, 1359. Muller, T.; Fernandez-Mayoralas, A.; Martín-Lomas, M. J. Chem. Soc., Chem. Commun. 1994, 775. Lin, C.-C.; Shimazaki, M.; Heck, M.-P.; Aoki, S.; Wang, R.; Kimura, T.; Ritzèn, H.; Takayama, S.; Wu, S.-H.; Weitz-Schmidt, G.; Wong, C.-H. J. Am. Chem. Soc. 1996, 118, 6826. Capozzi, G.; Dios, A.; Franck, R. W.; Geer, A.; Marzabadi, C.; Menichetti, S.; Nativi, C.; Tamarez, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 777. Marzabadi, C. H.; Franck, R. W. Chem. Commun. 1996, 2651. Fraser-Reid, B. Acc. Chem. Res. 1996, 29, 57. Liu, K. K.-C.; Danishefsky, S. J. Chem. Eur. J. 1996, 2, 1359. Dondoni, A.; Marra, A.; Rojo, I.; Scherrmann, M.-C. Tetrahedron 1996, 52, 3057. Seeberger, P. H.; Beebe, X.; Sukenick, G. D.; Pochapsky, S.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 491.
14. (b) For innovative methods, see: Boger, D. L.; Honda, T. J. Am. Chem. Soc. 1994, 116, 5647. Kondo, H.; Aoki, S.; Ichikawa, Y.; Halcomb, R. L.; Ritzen, H.; Wong, C.-H. J. Org. Chem. 1994, 59, 864. Nuller, T.; Schneider, R.; Schmidt, R. R. Tetrahedron Lett. 1994, 35, 4763. Watanabe, Y.; Nakamoto, C.; Yammamoto, S.; Ozaki, S. Tetrahedron 1994, 50, 6523. Yamanoi, T.; Nakamura, K.; Takeyama, H.; Yanagihara, Y. Bull. Chem. Soc. Jpn 1994, 67, 1359. Muller, T.; Fernandez-Mayoralas, A.; Martín-Lomas, M. J. Chem. Soc., Chem. Commun. 1994, 775. Lin, C.-C.; Shimazaki, M.; Heck, M.-P.; Aoki, S.; Wang, R.; Kimura, T.; Ritzèn, H.; Takayama, S.; Wu, S.-H.; Weitz-Schmidt, G.; Wong, C.-H. J. Am. Chem. Soc. 1996, 118, 6826. Capozzi, G.; Dios, A.; Franck, R. W.; Geer, A.; Marzabadi, C.; Menichetti, S.; Nativi, C.; Tamarez, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 777. Marzabadi, C. H.; Franck, R. W. Chem. Commun. 1996, 2651. Fraser-Reid, B. Acc. Chem. Res. 1996, 29, 57. Liu, K. K.-C.; Danishefsky, S. J. Chem. Eur. J. 1996, 2, 1359. Dondoni, A.; Marra, A.; Rojo, I.; Scherrmann, M.-C. Tetrahedron 1996, 52, 3057. Seeberger, P. H.; Beebe, X.; Sukenick, G. D.; Pochapsky, S.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 491.
15. (b) For innovative methods, see: Boger, D. L.; Honda, T. J. Am. Chem. Soc. 1994, 116, 5647. Kondo, H.; Aoki, S.; Ichikawa, Y.; Halcomb, R. L.; Ritzen, H.; Wong, C.-H. J. Org. Chem. 1994, 59, 864. Nuller, T.; Schneider, R.; Schmidt, R. R. Tetrahedron Lett. 1994, 35, 4763. Watanabe, Y.; Nakamoto, C.; Yammamoto, S.; Ozaki, S. Tetrahedron 1994, 50, 6523. Yamanoi, T.; Nakamura, K.; Takeyama, H.; Yanagihara, Y. Bull. Chem. Soc. Jpn 1994, 67, 1359. Muller, T.; Fernandez-Mayoralas, A.; Martín-Lomas, M. J. Chem. Soc., Chem. Commun. 1994, 775. Lin, C.-C.; Shimazaki, M.; Heck, M.-P.; Aoki, S.; Wang, R.; Kimura, T.; Ritzèn, H.; Takayama, S.; Wu, S.-H.; Weitz-Schmidt, G.; Wong, C.-H. J. Am. Chem. Soc. 1996, 118, 6826. Capozzi, G.; Dios, A.; Franck, R. W.; Geer, A.; Marzabadi, C.; Menichetti, S.; Nativi, C.; Tamarez, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 777. Marzabadi, C. H.; Franck, R. W. Chem. Commun. 1996, 2651. Fraser-Reid, B. Acc. Chem. Res. 1996, 29, 57. Liu, K. K.-C.; Danishefsky, S. J. Chem. Eur. J. 1996, 2, 1359. Dondoni, A.; Marra, A.; Rojo, I.; Scherrmann, M.-C. Tetrahedron 1996, 52, 3057. Seeberger, P. H.; Beebe, X.; Sukenick, G. D.; Pochapsky, S.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 491.
16. (b) For innovative methods, see: Boger, D. L.; Honda, T. J. Am. Chem. Soc. 1994, 116, 5647. Kondo, H.; Aoki, S.; Ichikawa, Y.; Halcomb, R. L.; Ritzen, H.; Wong, C.-H. J. Org. Chem. 1994, 59, 864. Nuller, T.; Schneider, R.; Schmidt, R. R. Tetrahedron Lett. 1994, 35, 4763. Watanabe, Y.; Nakamoto, C.; Yammamoto, S.; Ozaki, S. Tetrahedron 1994, 50, 6523. Yamanoi, T.; Nakamura, K.; Takeyama, H.; Yanagihara, Y. Bull. Chem. Soc. Jpn 1994, 67, 1359. Muller, T.; Fernandez-Mayoralas, A.; Martín-Lomas, M. J. Chem. Soc., Chem. Commun. 1994, 775. Lin, C.-C.; Shimazaki, M.; Heck, M.-P.; Aoki, S.; Wang, R.; Kimura, T.; Ritzèn, H.; Takayama, S.; Wu, S.-H.; Weitz-Schmidt, G.; Wong, C.-H. J. Am. Chem. Soc. 1996, 118, 6826. Capozzi, G.; Dios, A.; Franck, R. W.; Geer, A.; Marzabadi, C.; Menichetti, S.; Nativi, C.; Tamarez, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 777. Marzabadi, C. H.; Franck, R. W. Chem. Commun. 1996, 2651. Fraser-Reid, B. Acc. Chem. Res. 1996, 29, 57. Liu, K. K.-C.; Danishefsky, S. J. Chem. Eur. J. 1996, 2, 1359. Dondoni, A.; Marra, A.; Rojo, I.; Scherrmann, M.-C. Tetrahedron 1996, 52, 3057. Seeberger, P. H.; Beebe, X.; Sukenick, G. D.; Pochapsky, S.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 491.
17. (b) For innovative methods, see: Boger, D. L.; Honda, T. J. Am. Chem. Soc. 1994, 116, 5647. Kondo, H.; Aoki, S.; Ichikawa, Y.; Halcomb, R. L.; Ritzen, H.; Wong, C.-H. J. Org. Chem. 1994, 59, 864. Nuller, T.; Schneider, R.; Schmidt, R. R. Tetrahedron Lett. 1994, 35, 4763. Watanabe, Y.; Nakamoto, C.; Yammamoto, S.; Ozaki, S. Tetrahedron 1994, 50, 6523. Yamanoi, T.; Nakamura, K.; Takeyama, H.; Yanagihara, Y. Bull. Chem. Soc. Jpn 1994, 67, 1359. Muller, T.; Fernandez-Mayoralas, A.; Martín-Lomas, M. J. Chem. Soc., Chem. Commun. 1994, 775. Lin, C.-C.; Shimazaki, M.; Heck, M.-P.; Aoki, S.; Wang, R.; Kimura, T.; Ritzèn, H.; Takayama, S.; Wu, S.-H.; Weitz-Schmidt, G.; Wong, C.-H. J. Am. Chem. Soc. 1996, 118, 6826. Capozzi, G.; Dios, A.; Franck, R. W.; Geer, A.; Marzabadi, C.; Menichetti, S.; Nativi, C.; Tamarez, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 777. Marzabadi, C. H.; Franck, R. W. Chem. Commun. 1996, 2651. Fraser-Reid, B. Acc. Chem. Res. 1996, 29, 57. Liu, K. K.-C.; Danishefsky, S. J. Chem. Eur. J. 1996, 2, 1359. Dondoni, A.; Marra, A.; Rojo, I.; Scherrmann, M.-C. Tetrahedron 1996, 52, 3057. Seeberger, P. H.; Beebe, X.; Sukenick, G. D.; Pochapsky, S.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 491.
18. (b) For innovative methods, see: Boger, D. L.; Honda, T. J. Am. Chem. Soc. 1994, 116, 5647. Kondo, H.; Aoki, S.; Ichikawa, Y.; Halcomb, R. L.; Ritzen, H.; Wong, C.-H. J. Org. Chem. 1994, 59, 864. Nuller, T.; Schneider, R.; Schmidt, R. R. Tetrahedron Lett. 1994, 35, 4763. Watanabe, Y.; Nakamoto, C.; Yammamoto, S.; Ozaki, S. Tetrahedron 1994, 50, 6523. Yamanoi, T.; Nakamura, K.; Takeyama, H.; Yanagihara, Y. Bull. Chem. Soc. Jpn 1994, 67, 1359. Muller, T.; Fernandez-Mayoralas, A.; Martín-Lomas, M. J. Chem. Soc., Chem. Commun. 1994, 775. Lin, C.-C.; Shimazaki, M.; Heck, M.-P.; Aoki, S.; Wang, R.; Kimura, T.; Ritzèn, H.; Takayama, S.; Wu, S.-H.; Weitz-Schmidt, G.; Wong, C.-H. J. Am. Chem. Soc. 1996, 118, 6826. Capozzi, G.; Dios, A.; Franck, R. W.; Geer, A.; Marzabadi, C.; Menichetti, S.; Nativi, C.; Tamarez, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 777. Marzabadi, C. H.; Franck, R. W. Chem. Commun. 1996, 2651. Fraser-Reid, B. Acc. Chem. Res. 1996, 29, 57. Liu, K. K.-C.; Danishefsky, S. J. Chem. Eur. J. 1996, 2, 1359. Dondoni, A.; Marra, A.; Rojo, I.; Scherrmann, M.-C. Tetrahedron 1996, 52, 3057. Seeberger, P. H.; Beebe, X.; Sukenick, G. D.; Pochapsky, S.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 491.
19. (b) For innovative methods, see: Boger, D. L.; Honda, T. J. Am. Chem. Soc. 1994, 116, 5647. Kondo, H.; Aoki, S.; Ichikawa, Y.; Halcomb, R. L.; Ritzen, H.; Wong, C.-H. J. Org. Chem. 1994, 59, 864. Nuller, T.; Schneider, R.; Schmidt, R. R. Tetrahedron Lett. 1994, 35, 4763. Watanabe, Y.; Nakamoto, C.; Yammamoto, S.; Ozaki, S. Tetrahedron 1994, 50, 6523. Yamanoi, T.; Nakamura, K.; Takeyama, H.; Yanagihara, Y. Bull. Chem. Soc. Jpn 1994, 67, 1359. Muller, T.; Fernandez-Mayoralas, A.; Martín-Lomas, M. J. Chem. Soc., Chem. Commun. 1994, 775. Lin, C.-C.; Shimazaki, M.; Heck, M.-P.; Aoki, S.; Wang, R.; Kimura, T.; Ritzèn, H.; Takayama, S.; Wu, S.-H.; Weitz-Schmidt, G.; Wong, C.-H. J. Am. Chem. Soc. 1996, 118, 6826. Capozzi, G.; Dios, A.; Franck, R. W.; Geer, A.; Marzabadi, C.; Menichetti, S.; Nativi, C.; Tamarez, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 777. Marzabadi, C. H.; Franck, R. W. Chem. Commun. 1996, 2651. Fraser-Reid, B. Acc. Chem. Res. 1996, 29, 57. Liu, K. K.-C.; Danishefsky, S. J. Chem. Eur. J. 1996, 2, 1359. Dondoni, A.; Marra, A.; Rojo, I.; Scherrmann, M.-C. Tetrahedron 1996, 52, 3057. Seeberger, P. H.; Beebe, X.; Sukenick, G. D.; Pochapsky, S.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 491.
20. (b) For innovative methods, see: Boger, D. L.; Honda, T. J. Am. Chem. Soc. 1994, 116, 5647. Kondo, H.; Aoki, S.; Ichikawa, Y.; Halcomb, R. L.; Ritzen, H.; Wong, C.-H. J. Org. Chem. 1994, 59, 864. Nuller, T.; Schneider, R.; Schmidt, R. R. Tetrahedron Lett. 1994, 35, 4763. Watanabe, Y.; Nakamoto, C.; Yammamoto, S.; Ozaki, S. Tetrahedron 1994, 50, 6523. Yamanoi, T.; Nakamura, K.; Takeyama, H.; Yanagihara, Y. Bull. Chem. Soc. Jpn 1994, 67, 1359. Muller, T.; Fernandez-Mayoralas, A.; Martín-Lomas, M. J. Chem. Soc., Chem. Commun. 1994, 775. Lin, C.-C.; Shimazaki, M.; Heck, M.-P.; Aoki, S.; Wang, R.; Kimura, T.; Ritzèn, H.; Takayama, S.; Wu, S.-H.; Weitz-Schmidt, G.; Wong, C.-H. J. Am. Chem. Soc. 1996, 118, 6826. Capozzi, G.; Dios, A.; Franck, R. W.; Geer, A.; Marzabadi, C.; Menichetti, S.; Nativi, C.; Tamarez, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 777. Marzabadi, C. H.; Franck, R. W. Chem. Commun. 1996, 2651. Fraser-Reid, B. Acc. Chem. Res. 1996, 29, 57. Liu, K. K.-C.; Danishefsky, S. J. Chem. Eur. J. 1996, 2, 1359. Dondoni, A.; Marra, A.; Rojo, I.; Scherrmann, M.-C. Tetrahedron 1996, 52, 3057. Seeberger, P. H.; Beebe, X.; Sukenick, G. D.; Pochapsky, S.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 491.
21. (b) For innovative methods, see: Boger, D. L.; Honda, T. J. Am. Chem. Soc. 1994, 116, 5647. Kondo, H.; Aoki, S.; Ichikawa, Y.; Halcomb, R. L.; Ritzen, H.; Wong, C.-H. J. Org. Chem. 1994, 59, 864. Nuller, T.; Schneider, R.; Schmidt, R. R. Tetrahedron Lett. 1994, 35, 4763. Watanabe, Y.; Nakamoto, C.; Yammamoto, S.; Ozaki, S. Tetrahedron 1994, 50, 6523. Yamanoi, T.; Nakamura, K.; Takeyama, H.; Yanagihara, Y. Bull. Chem. Soc. Jpn 1994, 67, 1359. Muller, T.; Fernandez-Mayoralas, A.; Martín-Lomas, M. J. Chem. Soc., Chem. Commun. 1994, 775. Lin, C.-C.; Shimazaki, M.; Heck, M.-P.; Aoki, S.; Wang, R.; Kimura, T.; Ritzèn, H.; Takayama, S.; Wu, S.-H.; Weitz-Schmidt, G.; Wong, C.-H. J. Am. Chem. Soc. 1996, 118, 6826. Capozzi, G.; Dios, A.; Franck, R. W.; Geer, A.; Marzabadi, C.; Menichetti, S.; Nativi, C.; Tamarez, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 777. Marzabadi, C. H.; Franck, R. W. Chem. Commun. 1996, 2651. Fraser-Reid, B. Acc. Chem. Res. 1996, 29, 57. Liu, K. K.-C.; Danishefsky, S. J. Chem. Eur. J. 1996, 2, 1359. Dondoni, A.; Marra, A.; Rojo, I.; Scherrmann, M.-C. Tetrahedron 1996, 52, 3057. Seeberger, P. H.; Beebe, X.; Sukenick, G. D.; Pochapsky, S.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 491.
22. (b) For innovative methods, see: Boger, D. L.; Honda, T. J. Am. Chem. Soc. 1994, 116, 5647. Kondo, H.; Aoki, S.; Ichikawa, Y.; Halcomb, R. L.; Ritzen, H.; Wong, C.-H. J. Org. Chem. 1994, 59, 864. Nuller, T.; Schneider, R.; Schmidt, R. R. Tetrahedron Lett. 1994, 35, 4763. Watanabe, Y.; Nakamoto, C.; Yammamoto, S.; Ozaki, S. Tetrahedron 1994, 50, 6523. Yamanoi, T.; Nakamura, K.; Takeyama, H.; Yanagihara, Y. Bull. Chem. Soc. Jpn 1994, 67, 1359. Muller, T.; Fernandez-Mayoralas, A.; Martín-Lomas, M. J. Chem. Soc., Chem. Commun. 1994, 775. Lin, C.-C.; Shimazaki, M.; Heck, M.-P.; Aoki, S.; Wang, R.; Kimura, T.; Ritzèn, H.; Takayama, S.; Wu, S.-H.; Weitz-Schmidt, G.; Wong, C.-H. J. Am. Chem. Soc. 1996, 118, 6826. Capozzi, G.; Dios, A.; Franck, R. W.; Geer, A.; Marzabadi, C.; Menichetti, S.; Nativi, C.; Tamarez, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 777. Marzabadi, C. H.; Franck, R. W. Chem. Commun. 1996, 2651. Fraser-Reid, B. Acc. Chem. Res. 1996, 29, 57. Liu, K. K.-C.; Danishefsky, S. J. Chem. Eur. J. 1996, 2, 1359. Dondoni, A.; Marra, A.; Rojo, I.; Scherrmann, M.-C. Tetrahedron 1996, 52, 3057. Seeberger, P. H.; Beebe, X.; Sukenick, G. D.; Pochapsky, S.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 491.
23. (b) For innovative methods, see: Boger, D. L.; Honda, T. J. Am. Chem. Soc. 1994, 116, 5647. Kondo, H.; Aoki, S.; Ichikawa, Y.; Halcomb, R. L.; Ritzen, H.; Wong, C.-H. J. Org. Chem. 1994, 59, 864. Nuller, T.; Schneider, R.; Schmidt, R. R. Tetrahedron Lett. 1994, 35, 4763. Watanabe, Y.; Nakamoto, C.; Yammamoto, S.; Ozaki, S. Tetrahedron 1994, 50, 6523. Yamanoi, T.; Nakamura, K.; Takeyama, H.; Yanagihara, Y. Bull. Chem. Soc. Jpn 1994, 67, 1359. Muller, T.; Fernandez-Mayoralas, A.; Martín-Lomas, M. J. Chem. Soc., Chem. Commun. 1994, 775. Lin, C.-C.; Shimazaki, M.; Heck, M.-P.; Aoki, S.; Wang, R.; Kimura, T.; Ritzèn, H.; Takayama, S.; Wu, S.-H.; Weitz-Schmidt, G.; Wong, C.-H. J. Am. Chem. Soc. 1996, 118, 6826. Capozzi, G.; Dios, A.; Franck, R. W.; Geer, A.; Marzabadi, C.; Menichetti, S.; Nativi, C.; Tamarez, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 777. Marzabadi, C. H.; Franck, R. W. Chem. Commun. 1996, 2651. Fraser-Reid, B. Acc. Chem. Res. 1996, 29, 57. Liu, K. K.-C.; Danishefsky, S. J. Chem. Eur. J. 1996, 2, 1359. Dondoni, A.; Marra, A.; Rojo, I.; Scherrmann, M.-C. Tetrahedron 1996, 52, 3057. Seeberger, P. H.; Beebe, X.; Sukenick, G. D.; Pochapsky, S.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 491.
24. (b) For innovative methods, see: Boger, D. L.; Honda, T. J. Am. Chem. Soc. 1994, 116, 5647. Kondo, H.; Aoki, S.; Ichikawa, Y.; Halcomb, R. L.; Ritzen, H.; Wong, C.-H. J. Org. Chem. 1994, 59, 864. Nuller, T.; Schneider, R.; Schmidt, R. R. Tetrahedron Lett. 1994, 35, 4763. Watanabe, Y.; Nakamoto, C.; Yammamoto, S.; Ozaki, S. Tetrahedron 1994, 50, 6523. Yamanoi, T.; Nakamura, K.; Takeyama, H.; Yanagihara, Y. Bull. Chem. Soc. Jpn 1994, 67, 1359. Muller, T.; Fernandez-Mayoralas, A.; Martín-Lomas, M. J. Chem. Soc., Chem. Commun. 1994, 775. Lin, C.-C.; Shimazaki, M.; Heck, M.-P.; Aoki, S.; Wang, R.; Kimura, T.; Ritzèn, H.; Takayama, S.; Wu, S.-H.; Weitz-Schmidt, G.; Wong, C.-H. J. Am. Chem. Soc. 1996, 118, 6826. Capozzi, G.; Dios, A.; Franck, R. W.; Geer, A.; Marzabadi, C.; Menichetti, S.; Nativi, C.; Tamarez, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 777. Marzabadi, C. H.; Franck, R. W. Chem. Commun. 1996, 2651. Fraser-Reid, B. Acc. Chem. Res. 1996, 29, 57. Liu, K. K.-C.; Danishefsky, S. J. Chem. Eur. J. 1996, 2, 1359. Dondoni, A.; Marra, A.; Rojo, I.; Scherrmann, M.-C. Tetrahedron 1996, 52, 3057. Seeberger, P. H.; Beebe, X.; Sukenick, G. D.; Pochapsky, S.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 491.
25. (b) For innovative methods, see: Boger, D. L.; Honda, T. J. Am. Chem. Soc. 1994, 116, 5647. Kondo, H.; Aoki, S.; Ichikawa, Y.; Halcomb, R. L.; Ritzen, H.; Wong, C.-H. J. Org. Chem. 1994, 59, 864. Nuller, T.; Schneider, R.; Schmidt, R. R. Tetrahedron Lett. 1994, 35, 4763. Watanabe, Y.; Nakamoto, C.; Yammamoto, S.; Ozaki, S. Tetrahedron 1994, 50, 6523. Yamanoi, T.; Nakamura, K.; Takeyama, H.; Yanagihara, Y. Bull. Chem. Soc. Jpn 1994, 67, 1359. Muller, T.; Fernandez-Mayoralas, A.; Martín-Lomas, M. J. Chem. Soc., Chem. Commun. 1994, 775. Lin, C.-C.; Shimazaki, M.; Heck, M.-P.; Aoki, S.; Wang, R.; Kimura, T.; Ritzèn, H.; Takayama, S.; Wu, S.-H.; Weitz-Schmidt, G.; Wong, C.-H. J. Am. Chem. Soc. 1996, 118, 6826. Capozzi, G.; Dios, A.; Franck, R. W.; Geer, A.; Marzabadi, C.; Menichetti, S.; Nativi, C.; Tamarez, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 777. Marzabadi, C. H.; Franck, R. W. Chem. Commun. 1996, 2651. Fraser-Reid, B. Acc. Chem. Res. 1996, 29, 57. Liu, K. K.-C.; Danishefsky, S. J. Chem. Eur. J. 1996, 2, 1359. Dondoni, A.; Marra, A.; Rojo, I.; Scherrmann, M.-C. Tetrahedron 1996, 52, 3057. Seeberger, P. H.; Beebe, X.; Sukenick, G. D.; Pochapsky, S.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 491.
26. Postema, M. H. D. In C-Glycoside Synthesis; Rees, C. W., Ed.; CRC Press, Inc.: Boca Raton, 1995. Levy, D. E.; Tang, C. In The Chemistry of C-glycosides; Baldwin, J. E., Magnus, P. D., Eds.; Elsevier Science Ltd: Oxford, 1995.
27. Postema, M. H. D. In C-Glycoside Synthesis; Rees, C. W., Ed.; CRC Press, Inc.: Boca Raton, 1995. Levy, D. E.; Tang, C. In The Chemistry of C-glycosides; Baldwin, J. E., Magnus, P. D., Eds.; Elsevier Science Ltd: Oxford, 1995.
28. For selected recent papers, see: (a) Vauzeilles, B.; Cravo, D.; Mallet, J.-M.; Sinaÿ, P. Synlett 1993, 552. Xin, Y. C.; Mallet, J.-M.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1993, 864. Mallet, A.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1994, 5, 2593. Chénedé, A.; Perrin, E.; Rekaï, E. D.; Sinaÿ, P. Synlett 1994, 420. (b) Johnson, C. R.; Miller, M. W.; Golebiowski, A.; Sundram, H.; Ksebati, M. B. Tetrahedron Lett. 1994, 35, 8991. (c) Ferritto, R.; Vogel, P. Tetrahedron: Asymmetry 1994, 5, 2077. (d) Paton, R. M.; Penman, K. J. Tetrahedron Lett. 1994, 35, 3163. (e) Armstrong, R. W.; Sutherlin, D. P. Tetrahedron Lett. 1994, 35, 7743. (f) Lay, L. Nicotra, F.; Pangrazio, C.; Panza, L.; Russo, G. J. Chem. Soc., Perkin Trans. 1 1994, 333. (g) Dietrich, H.; Schmidt, R. R. Liebigs Ann. Chem. 1994, 975. (h) Mazéas, D.; Skrydstrup, T.; Doumeix, O.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1383. Mazéas, D.; Skrydstrup, T.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1995, 34, 909. (i) Eyrisch, O.; Fessner, W.-D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1639. (j) Sutherlin, D. P.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 9802. (k) Wong, C.-H.; Hung, S.-C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2671. (l) Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. J. 1996, 2, 502. (m) Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894. (n) Dondoni, A.; Boscarato, A.; Zuurmond, H.-M. Tetrahedron Lett. 1996, 37, 7587. (o) Martin, O. R.; Liu, L.; Yang, F. Tetrahedron Lett. 1996, 37, 1991. (p) Baudat, A.; Vogel, P. Tetrahedron Lett. 1996, 37, 483. (q) Vlahov, I. R.; Vlahova, P. I.; Linhardt, R. J. J. Am. Chem. Soc. 1997, 119, 1480. (r) Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215. (s) Dondoni, A.; Kniezo, L.; Martinkova, M.; Imrich, J. Chem. Eur. J. 1997, 3, 424.
29. For selected recent papers, see: (a) Vauzeilles, B.; Cravo, D.; Mallet, J.-M.; Sinaÿ, P. Synlett 1993, 552. Xin, Y. C.; Mallet, J.-M.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1993, 864. Mallet, A.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1994, 5, 2593. Chénedé, A.; Perrin, E.; Rekaï, E. D.; Sinaÿ, P. Synlett 1994, 420. (b) Johnson, C. R.; Miller, M. W.; Golebiowski, A.; Sundram, H.; Ksebati, M. B. Tetrahedron Lett. 1994, 35, 8991. (c) Ferritto, R.; Vogel, P. Tetrahedron: Asymmetry 1994, 5, 2077. (d) Paton, R. M.; Penman, K. J. Tetrahedron Lett. 1994, 35, 3163. (e) Armstrong, R. W.; Sutherlin, D. P. Tetrahedron Lett. 1994, 35, 7743. (f) Lay, L. Nicotra, F.; Pangrazio, C.; Panza, L.; Russo, G. J. Chem. Soc., Perkin Trans. 1 1994, 333. (g) Dietrich, H.; Schmidt, R. R. Liebigs Ann. Chem. 1994, 975. (h) Mazéas, D.; Skrydstrup, T.; Doumeix, O.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1383. Mazéas, D.; Skrydstrup, T.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1995, 34, 909. (i) Eyrisch, O.; Fessner, W.-D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1639. (j) Sutherlin, D. P.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 9802. (k) Wong, C.-H.; Hung, S.-C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2671. (l) Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. J. 1996, 2, 502. (m) Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894. (n) Dondoni, A.; Boscarato, A.; Zuurmond, H.-M. Tetrahedron Lett. 1996, 37, 7587. (o) Martin, O. R.; Liu, L.; Yang, F. Tetrahedron Lett. 1996, 37, 1991. (p) Baudat, A.; Vogel, P. Tetrahedron Lett. 1996, 37, 483. (q) Vlahov, I. R.; Vlahova, P. I.; Linhardt, R. J. J. Am. Chem. Soc. 1997, 119, 1480. (r) Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215. (s) Dondoni, A.; Kniezo, L.; Martinkova, M.; Imrich, J. Chem. Eur. J. 1997, 3, 424.
30. For selected recent papers, see: (a) Vauzeilles, B.; Cravo, D.; Mallet, J.-M.; Sinaÿ, P. Synlett 1993, 552. Xin, Y. C.; Mallet, J.-M.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1993, 864. Mallet, A.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1994, 5, 2593. Chénedé, A.; Perrin, E.; Rekaï, E. D.; Sinaÿ, P. Synlett 1994, 420. (b) Johnson, C. R.; Miller, M. W.; Golebiowski, A.; Sundram, H.; Ksebati, M. B. Tetrahedron Lett. 1994, 35, 8991. (c) Ferritto, R.; Vogel, P. Tetrahedron: Asymmetry 1994, 5, 2077. (d) Paton, R. M.; Penman, K. J. Tetrahedron Lett. 1994, 35, 3163. (e) Armstrong, R. W.; Sutherlin, D. P. Tetrahedron Lett. 1994, 35, 7743. (f) Lay, L. Nicotra, F.; Pangrazio, C.; Panza, L.; Russo, G. J. Chem. Soc., Perkin Trans. 1 1994, 333. (g) Dietrich, H.; Schmidt, R. R. Liebigs Ann. Chem. 1994, 975. (h) Mazéas, D.; Skrydstrup, T.; Doumeix, O.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1383. Mazéas, D.; Skrydstrup, T.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1995, 34, 909. (i) Eyrisch, O.; Fessner, W.-D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1639. (j) Sutherlin, D. P.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 9802. (k) Wong, C.-H.; Hung, S.-C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2671. (l) Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. J. 1996, 2, 502. (m) Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894. (n) Dondoni, A.; Boscarato, A.; Zuurmond, H.-M. Tetrahedron Lett. 1996, 37, 7587. (o) Martin, O. R.; Liu, L.; Yang, F. Tetrahedron Lett. 1996, 37, 1991. (p) Baudat, A.; Vogel, P. Tetrahedron Lett. 1996, 37, 483. (q) Vlahov, I. R.; Vlahova, P. I.; Linhardt, R. J. J. Am. Chem. Soc. 1997, 119, 1480. (r) Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215. (s) Dondoni, A.; Kniezo, L.; Martinkova, M.; Imrich, J. Chem. Eur. J. 1997, 3, 424.
31. For selected recent papers, see: (a) Vauzeilles, B.; Cravo, D.; Mallet, J.-M.; Sinaÿ, P. Synlett 1993, 552. Xin, Y. C.; Mallet, J.-M.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1993, 864. Mallet, A.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1994, 5, 2593. Chénedé, A.; Perrin, E.; Rekaï, E. D.; Sinaÿ, P. Synlett 1994, 420. (b) Johnson, C. R.; Miller, M. W.; Golebiowski, A.; Sundram, H.; Ksebati, M. B. Tetrahedron Lett. 1994, 35, 8991. (c) Ferritto, R.; Vogel, P. Tetrahedron: Asymmetry 1994, 5, 2077. (d) Paton, R. M.; Penman, K. J. Tetrahedron Lett. 1994, 35, 3163. (e) Armstrong, R. W.; Sutherlin, D. P. Tetrahedron Lett. 1994, 35, 7743. (f) Lay, L. Nicotra, F.; Pangrazio, C.; Panza, L.; Russo, G. J. Chem. Soc., Perkin Trans. 1 1994, 333. (g) Dietrich, H.; Schmidt, R. R. Liebigs Ann. Chem. 1994, 975. (h) Mazéas, D.; Skrydstrup, T.; Doumeix, O.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1383. Mazéas, D.; Skrydstrup, T.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1995, 34, 909. (i) Eyrisch, O.; Fessner, W.-D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1639. (j) Sutherlin, D. P.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 9802. (k) Wong, C.-H.; Hung, S.-C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2671. (l) Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. J. 1996, 2, 502. (m) Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894. (n) Dondoni, A.; Boscarato, A.; Zuurmond, H.-M. Tetrahedron Lett. 1996, 37, 7587. (o) Martin, O. R.; Liu, L.; Yang, F. Tetrahedron Lett. 1996, 37, 1991. (p) Baudat, A.; Vogel, P. Tetrahedron Lett. 1996, 37, 483. (q) Vlahov, I. R.; Vlahova, P. I.; Linhardt, R. J. J. Am. Chem. Soc. 1997, 119, 1480. (r) Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215. (s) Dondoni, A.; Kniezo, L.; Martinkova, M.; Imrich, J. Chem. Eur. J. 1997, 3, 424.
32. For selected recent papers, see: (a) Vauzeilles, B.; Cravo, D.; Mallet, J.-M.; Sinaÿ, P. Synlett 1993, 552. Xin, Y. C.; Mallet, J.-M.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1993, 864. Mallet, A.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1994, 5, 2593. Chénedé, A.; Perrin, E.; Rekaï, E. D.; Sinaÿ, P. Synlett 1994, 420. (b) Johnson, C. R.; Miller, M. W.; Golebiowski, A.; Sundram, H.; Ksebati, M. B. Tetrahedron Lett. 1994, 35, 8991. (c) Ferritto, R.; Vogel, P. Tetrahedron: Asymmetry 1994, 5, 2077. (d) Paton, R. M.; Penman, K. J. Tetrahedron Lett. 1994, 35, 3163. (e) Armstrong, R. W.; Sutherlin, D. P. Tetrahedron Lett. 1994, 35, 7743. (f) Lay, L. Nicotra, F.; Pangrazio, C.; Panza, L.; Russo, G. J. Chem. Soc., Perkin Trans. 1 1994, 333. (g) Dietrich, H.; Schmidt, R. R. Liebigs Ann. Chem. 1994, 975. (h) Mazéas, D.; Skrydstrup, T.; Doumeix, O.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1383. Mazéas, D.; Skrydstrup, T.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1995, 34, 909. (i) Eyrisch, O.; Fessner, W.-D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1639. (j) Sutherlin, D. P.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 9802. (k) Wong, C.-H.; Hung, S.-C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2671. (l) Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. J. 1996, 2, 502. (m) Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894. (n) Dondoni, A.; Boscarato, A.; Zuurmond, H.-M. Tetrahedron Lett. 1996, 37, 7587. (o) Martin, O. R.; Liu, L.; Yang, F. Tetrahedron Lett. 1996, 37, 1991. (p) Baudat, A.; Vogel, P. Tetrahedron Lett. 1996, 37, 483. (q) Vlahov, I. R.; Vlahova, P. I.; Linhardt, R. J. J. Am. Chem. Soc. 1997, 119, 1480. (r) Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215. (s) Dondoni, A.; Kniezo, L.; Martinkova, M.; Imrich, J. Chem. Eur. J. 1997, 3, 424.
33. For selected recent papers, see: (a) Vauzeilles, B.; Cravo, D.; Mallet, J.-M.; Sinaÿ, P. Synlett 1993, 552. Xin, Y. C.; Mallet, J.-M.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1993, 864. Mallet, A.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1994, 5, 2593. Chénedé, A.; Perrin, E.; Rekaï, E. D.; Sinaÿ, P. Synlett 1994, 420. (b) Johnson, C. R.; Miller, M. W.; Golebiowski, A.; Sundram, H.; Ksebati, M. B. Tetrahedron Lett. 1994, 35, 8991. (c) Ferritto, R.; Vogel, P. Tetrahedron: Asymmetry 1994, 5, 2077. (d) Paton, R. M.; Penman, K. J. Tetrahedron Lett. 1994, 35, 3163. (e) Armstrong, R. W.; Sutherlin, D. P. Tetrahedron Lett. 1994, 35, 7743. (f) Lay, L. Nicotra, F.; Pangrazio, C.; Panza, L.; Russo, G. J. Chem. Soc., Perkin Trans. 1 1994, 333. (g) Dietrich, H.; Schmidt, R. R. Liebigs Ann. Chem. 1994, 975. (h) Mazéas, D.; Skrydstrup, T.; Doumeix, O.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1383. Mazéas, D.; Skrydstrup, T.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1995, 34, 909. (i) Eyrisch, O.; Fessner, W.-D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1639. (j) Sutherlin, D. P.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 9802. (k) Wong, C.-H.; Hung, S.-C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2671. (l) Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. J. 1996, 2, 502. (m) Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894. (n) Dondoni, A.; Boscarato, A.; Zuurmond, H.-M. Tetrahedron Lett. 1996, 37, 7587. (o) Martin, O. R.; Liu, L.; Yang, F. Tetrahedron Lett. 1996, 37, 1991. (p) Baudat, A.; Vogel, P. Tetrahedron Lett. 1996, 37, 483. (q) Vlahov, I. R.; Vlahova, P. I.; Linhardt, R. J. J. Am. Chem. Soc. 1997, 119, 1480. (r) Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215. (s) Dondoni, A.; Kniezo, L.; Martinkova, M.; Imrich, J. Chem. Eur. J. 1997, 3, 424.
34. For selected recent papers, see: (a) Vauzeilles, B.; Cravo, D.; Mallet, J.-M.; Sinaÿ, P. Synlett 1993, 552. Xin, Y. C.; Mallet, J.-M.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1993, 864. Mallet, A.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1994, 5, 2593. Chénedé, A.; Perrin, E.; Rekaï, E. D.; Sinaÿ, P. Synlett 1994, 420. (b) Johnson, C. R.; Miller, M. W.; Golebiowski, A.; Sundram, H.; Ksebati, M. B. Tetrahedron Lett. 1994, 35, 8991. (c) Ferritto, R.; Vogel, P. Tetrahedron: Asymmetry 1994, 5, 2077. (d) Paton, R. M.; Penman, K. J. Tetrahedron Lett. 1994, 35, 3163. (e) Armstrong, R. W.; Sutherlin, D. P. Tetrahedron Lett. 1994, 35, 7743. (f) Lay, L. Nicotra, F.; Pangrazio, C.; Panza, L.; Russo, G. J. Chem. Soc., Perkin Trans. 1 1994, 333. (g) Dietrich, H.; Schmidt, R. R. Liebigs Ann. Chem. 1994, 975. (h) Mazéas, D.; Skrydstrup, T.; Doumeix, O.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1383. Mazéas, D.; Skrydstrup, T.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1995, 34, 909. (i) Eyrisch, O.; Fessner, W.-D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1639. (j) Sutherlin, D. P.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 9802. (k) Wong, C.-H.; Hung, S.-C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2671. (l) Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. J. 1996, 2, 502. (m) Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894. (n) Dondoni, A.; Boscarato, A.; Zuurmond, H.-M. Tetrahedron Lett. 1996, 37, 7587. (o) Martin, O. R.; Liu, L.; Yang, F. Tetrahedron Lett. 1996, 37, 1991. (p) Baudat, A.; Vogel, P. Tetrahedron Lett. 1996, 37, 483. (q) Vlahov, I. R.; Vlahova, P. I.; Linhardt, R. J. J. Am. Chem. Soc. 1997, 119, 1480. (r) Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215. (s) Dondoni, A.; Kniezo, L.; Martinkova, M.; Imrich, J. Chem. Eur. J. 1997, 3, 424.
35. For selected recent papers, see: (a) Vauzeilles, B.; Cravo, D.; Mallet, J.-M.; Sinaÿ, P. Synlett 1993, 552. Xin, Y. C.; Mallet, J.-M.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1993, 864. Mallet, A.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1994, 5, 2593. Chénedé, A.; Perrin, E.; Rekaï, E. D.; Sinaÿ, P. Synlett 1994, 420. (b) Johnson, C. R.; Miller, M. W.; Golebiowski, A.; Sundram, H.; Ksebati, M. B. Tetrahedron Lett. 1994, 35, 8991. (c) Ferritto, R.; Vogel, P. Tetrahedron: Asymmetry 1994, 5, 2077. (d) Paton, R. M.; Penman, K. J. Tetrahedron Lett. 1994, 35, 3163. (e) Armstrong, R. W.; Sutherlin, D. P. Tetrahedron Lett. 1994, 35, 7743. (f) Lay, L. Nicotra, F.; Pangrazio, C.; Panza, L.; Russo, G. J. Chem. Soc., Perkin Trans. 1 1994, 333. (g) Dietrich, H.; Schmidt, R. R. Liebigs Ann. Chem. 1994, 975. (h) Mazéas, D.; Skrydstrup, T.; Doumeix, O.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1383. Mazéas, D.; Skrydstrup, T.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1995, 34, 909. (i) Eyrisch, O.; Fessner, W.-D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1639. (j) Sutherlin, D. P.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 9802. (k) Wong, C.-H.; Hung, S.-C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2671. (l) Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. J. 1996, 2, 502. (m) Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894. (n) Dondoni, A.; Boscarato, A.; Zuurmond, H.-M. Tetrahedron Lett. 1996, 37, 7587. (o) Martin, O. R.; Liu, L.; Yang, F. Tetrahedron Lett. 1996, 37, 1991. (p) Baudat, A.; Vogel, P. Tetrahedron Lett. 1996, 37, 483. (q) Vlahov, I. R.; Vlahova, P. I.; Linhardt, R. J. J. Am. Chem. Soc. 1997, 119, 1480. (r) Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215. (s) Dondoni, A.; Kniezo, L.; Martinkova, M.; Imrich, J. Chem. Eur. J. 1997, 3, 424.
36. For selected recent papers, see: (a) Vauzeilles, B.; Cravo, D.; Mallet, J.-M.; Sinaÿ, P. Synlett 1993, 552. Xin, Y. C.; Mallet, J.-M.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1993, 864. Mallet, A.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1994, 5, 2593. Chénedé, A.; Perrin, E.; Rekaï, E. D.; Sinaÿ, P. Synlett 1994, 420. (b) Johnson, C. R.; Miller, M. W.; Golebiowski, A.; Sundram, H.; Ksebati, M. B. Tetrahedron Lett. 1994, 35, 8991. (c) Ferritto, R.; Vogel, P. Tetrahedron: Asymmetry 1994, 5, 2077. (d) Paton, R. M.; Penman, K. J. Tetrahedron Lett. 1994, 35, 3163. (e) Armstrong, R. W.; Sutherlin, D. P. Tetrahedron Lett. 1994, 35, 7743. (f) Lay, L. Nicotra, F.; Pangrazio, C.; Panza, L.; Russo, G. J. Chem. Soc., Perkin Trans. 1 1994, 333. (g) Dietrich, H.; Schmidt, R. R. Liebigs Ann. Chem. 1994, 975. (h) Mazéas, D.; Skrydstrup, T.; Doumeix, O.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1383. Mazéas, D.; Skrydstrup, T.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1995, 34, 909. (i) Eyrisch, O.; Fessner, W.-D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1639. (j) Sutherlin, D. P.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 9802. (k) Wong, C.-H.; Hung, S.-C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2671. (l) Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. J. 1996, 2, 502. (m) Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894. (n) Dondoni, A.; Boscarato, A.; Zuurmond, H.-M. Tetrahedron Lett. 1996, 37, 7587. (o) Martin, O. R.; Liu, L.; Yang, F. Tetrahedron Lett. 1996, 37, 1991. (p) Baudat, A.; Vogel, P. Tetrahedron Lett. 1996, 37, 483. (q) Vlahov, I. R.; Vlahova, P. I.; Linhardt, R. J. J. Am. Chem. Soc. 1997, 119, 1480. (r) Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215. (s) Dondoni, A.; Kniezo, L.; Martinkova, M.; Imrich, J. Chem. Eur. J. 1997, 3, 424.
37. For selected recent papers, see: (a) Vauzeilles, B.; Cravo, D.; Mallet, J.-M.; Sinaÿ, P. Synlett 1993, 552. Xin, Y. C.; Mallet, J.-M.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1993, 864. Mallet, A.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1994, 5, 2593. Chénedé, A.; Perrin, E.; Rekaï, E. D.; Sinaÿ, P. Synlett 1994, 420. (b) Johnson, C. R.; Miller, M. W.; Golebiowski, A.; Sundram, H.; Ksebati, M. B. Tetrahedron Lett. 1994, 35, 8991. (c) Ferritto, R.; Vogel, P. Tetrahedron: Asymmetry 1994, 5, 2077. (d) Paton, R. M.; Penman, K. J. Tetrahedron Lett. 1994, 35, 3163. (e) Armstrong, R. W.; Sutherlin, D. P. Tetrahedron Lett. 1994, 35, 7743. (f) Lay, L. Nicotra, F.; Pangrazio, C.; Panza, L.; Russo, G. J. Chem. Soc., Perkin Trans. 1 1994, 333. (g) Dietrich, H.; Schmidt, R. R. Liebigs Ann. Chem. 1994, 975. (h) Mazéas, D.; Skrydstrup, T.; Doumeix, O.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1383. Mazéas, D.; Skrydstrup, T.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1995, 34, 909. (i) Eyrisch, O.; Fessner, W.-D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1639. (j) Sutherlin, D. P.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 9802. (k) Wong, C.-H.; Hung, S.-C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2671. (l) Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. J. 1996, 2, 502. (m) Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894. (n) Dondoni, A.; Boscarato, A.; Zuurmond, H.-M. Tetrahedron Lett. 1996, 37, 7587. (o) Martin, O. R.; Liu, L.; Yang, F. Tetrahedron Lett. 1996, 37, 1991. (p) Baudat, A.; Vogel, P. Tetrahedron Lett. 1996, 37, 483. (q) Vlahov, I. R.; Vlahova, P. I.; Linhardt, R. J. J. Am. Chem. Soc. 1997, 119, 1480. (r) Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215. (s) Dondoni, A.; Kniezo, L.; Martinkova, M.; Imrich, J. Chem. Eur. J. 1997, 3, 424.
38. For selected recent papers, see: (a) Vauzeilles, B.; Cravo, D.; Mallet, J.-M.; Sinaÿ, P. Synlett 1993, 552. Xin, Y. C.; Mallet, J.-M.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1993, 864. Mallet, A.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1994, 5, 2593. Chénedé, A.; Perrin, E.; Rekaï, E. D.; Sinaÿ, P. Synlett 1994, 420. (b) Johnson, C. R.; Miller, M. W.; Golebiowski, A.; Sundram, H.; Ksebati, M. B. Tetrahedron Lett. 1994, 35, 8991. (c) Ferritto, R.; Vogel, P. Tetrahedron: Asymmetry 1994, 5, 2077. (d) Paton, R. M.; Penman, K. J. Tetrahedron Lett. 1994, 35, 3163. (e) Armstrong, R. W.; Sutherlin, D. P. Tetrahedron Lett. 1994, 35, 7743. (f) Lay, L. Nicotra, F.; Pangrazio, C.; Panza, L.; Russo, G. J. Chem. Soc., Perkin Trans. 1 1994, 333. (g) Dietrich, H.; Schmidt, R. R. Liebigs Ann. Chem. 1994, 975. (h) Mazéas, D.; Skrydstrup, T.; Doumeix, O.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1383. Mazéas, D.; Skrydstrup, T.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1995, 34, 909. (i) Eyrisch, O.; Fessner, W.-D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1639. (j) Sutherlin, D. P.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 9802. (k) Wong, C.-H.; Hung, S.-C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2671. (l) Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. J. 1996, 2, 502. (m) Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894. (n) Dondoni, A.; Boscarato, A.; Zuurmond, H.-M. Tetrahedron Lett. 1996, 37, 7587. (o) Martin, O. R.; Liu, L.; Yang, F. Tetrahedron Lett. 1996, 37, 1991. (p) Baudat, A.; Vogel, P. Tetrahedron Lett. 1996, 37, 483. (q) Vlahov, I. R.; Vlahova, P. I.; Linhardt, R. J. J. Am. Chem. Soc. 1997, 119, 1480. (r) Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215. (s) Dondoni, A.; Kniezo, L.; Martinkova, M.; Imrich, J. Chem. Eur. J. 1997, 3, 424.
39. For selected recent papers, see: (a) Vauzeilles, B.; Cravo, D.; Mallet, J.-M.; Sinaÿ, P. Synlett 1993, 552. Xin, Y. C.; Mallet, J.-M.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1993, 864. Mallet, A.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1994, 5, 2593. Chénedé, A.; Perrin, E.; Rekaï, E. D.; Sinaÿ, P. Synlett 1994, 420. (b) Johnson, C. R.; Miller, M. W.; Golebiowski, A.; Sundram, H.; Ksebati, M. B. Tetrahedron Lett. 1994, 35, 8991. (c) Ferritto, R.; Vogel, P. Tetrahedron: Asymmetry 1994, 5, 2077. (d) Paton, R. M.; Penman, K. J. Tetrahedron Lett. 1994, 35, 3163. (e) Armstrong, R. W.; Sutherlin, D. P. Tetrahedron Lett. 1994, 35, 7743. (f) Lay, L. Nicotra, F.; Pangrazio, C.; Panza, L.; Russo, G. J. Chem. Soc., Perkin Trans. 1 1994, 333. (g) Dietrich, H.; Schmidt, R. R. Liebigs Ann. Chem. 1994, 975. (h) Mazéas, D.; Skrydstrup, T.; Doumeix, O.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1383. Mazéas, D.; Skrydstrup, T.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1995, 34, 909. (i) Eyrisch, O.; Fessner, W.-D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1639. (j) Sutherlin, D. P.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 9802. (k) Wong, C.-H.; Hung, S.-C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2671. (l) Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. J. 1996, 2, 502. (m) Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894. (n) Dondoni, A.; Boscarato, A.; Zuurmond, H.-M. Tetrahedron Lett. 1996, 37, 7587. (o) Martin, O. R.; Liu, L.; Yang, F. Tetrahedron Lett. 1996, 37, 1991. (p) Baudat, A.; Vogel, P. Tetrahedron Lett. 1996, 37, 483. (q) Vlahov, I. R.; Vlahova, P. I.; Linhardt, R. J. J. Am. Chem. Soc. 1997, 119, 1480. (r) Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215. (s) Dondoni, A.; Kniezo, L.; Martinkova, M.; Imrich, J. Chem. Eur. J. 1997, 3, 424.
40. For selected recent papers, see: (a) Vauzeilles, B.; Cravo, D.; Mallet, J.-M.; Sinaÿ, P. Synlett 1993, 552. Xin, Y. C.; Mallet, J.-M.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1993, 864. Mallet, A.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1994, 5, 2593. Chénedé, A.; Perrin, E.; Rekaï, E. D.; Sinaÿ, P. Synlett 1994, 420. (b) Johnson, C. R.; Miller, M. W.; Golebiowski, A.; Sundram, H.; Ksebati, M. B. Tetrahedron Lett. 1994, 35, 8991. (c) Ferritto, R.; Vogel, P. Tetrahedron: Asymmetry 1994, 5, 2077. (d) Paton, R. M.; Penman, K. J. Tetrahedron Lett. 1994, 35, 3163. (e) Armstrong, R. W.; Sutherlin, D. P. Tetrahedron Lett. 1994, 35, 7743. (f) Lay, L. Nicotra, F.; Pangrazio, C.; Panza, L.; Russo, G. J. Chem. Soc., Perkin Trans. 1 1994, 333. (g) Dietrich, H.; Schmidt, R. R. Liebigs Ann. Chem. 1994, 975. (h) Mazéas, D.; Skrydstrup, T.; Doumeix, O.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1383. Mazéas, D.; Skrydstrup, T.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1995, 34, 909. (i) Eyrisch, O.; Fessner, W.-D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1639. (j) Sutherlin, D. P.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 9802. (k) Wong, C.-H.; Hung, S.-C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2671. (l) Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. J. 1996, 2, 502. (m) Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894. (n) Dondoni, A.; Boscarato, A.; Zuurmond, H.-M. Tetrahedron Lett. 1996, 37, 7587. (o) Martin, O. R.; Liu, L.; Yang, F. Tetrahedron Lett. 1996, 37, 1991. (p) Baudat, A.; Vogel, P. Tetrahedron Lett. 1996, 37, 483. (q) Vlahov, I. R.; Vlahova, P. I.; Linhardt, R. J. J. Am. Chem. Soc. 1997, 119, 1480. (r) Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215. (s) Dondoni, A.; Kniezo, L.; Martinkova, M.; Imrich, J. Chem. Eur. J. 1997, 3, 424.
41. For selected recent papers, see: (a) Vauzeilles, B.; Cravo, D.; Mallet, J.-M.; Sinaÿ, P. Synlett 1993, 552. Xin, Y. C.; Mallet, J.-M.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1993, 864. Mallet, A.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1994, 5, 2593. Chénedé, A.; Perrin, E.; Rekaï, E. D.; Sinaÿ, P. Synlett 1994, 420. (b) Johnson, C. R.; Miller, M. W.; Golebiowski, A.; Sundram, H.; Ksebati, M. B. Tetrahedron Lett. 1994, 35, 8991. (c) Ferritto, R.; Vogel, P. Tetrahedron: Asymmetry 1994, 5, 2077. (d) Paton, R. M.; Penman, K. J. Tetrahedron Lett. 1994, 35, 3163. (e) Armstrong, R. W.; Sutherlin, D. P. Tetrahedron Lett. 1994, 35, 7743. (f) Lay, L. Nicotra, F.; Pangrazio, C.; Panza, L.; Russo, G. J. Chem. Soc., Perkin Trans. 1 1994, 333. (g) Dietrich, H.; Schmidt, R. R. Liebigs Ann. Chem. 1994, 975. (h) Mazéas, D.; Skrydstrup, T.; Doumeix, O.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1383. Mazéas, D.; Skrydstrup, T.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1995, 34, 909. (i) Eyrisch, O.; Fessner, W.-D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1639. (j) Sutherlin, D. P.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 9802. (k) Wong, C.-H.; Hung, S.-C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2671. (l) Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. J. 1996, 2, 502. (m) Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894. (n) Dondoni, A.; Boscarato, A.; Zuurmond, H.-M. Tetrahedron Lett. 1996, 37, 7587. (o) Martin, O. R.; Liu, L.; Yang, F. Tetrahedron Lett. 1996, 37, 1991. (p) Baudat, A.; Vogel, P. Tetrahedron Lett. 1996, 37, 483. (q) Vlahov, I. R.; Vlahova, P. I.; Linhardt, R. J. J. Am. Chem. Soc. 1997, 119, 1480. (r) Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215. (s) Dondoni, A.; Kniezo, L.; Martinkova, M.; Imrich, J. Chem. Eur. J. 1997, 3, 424.
42. For selected recent papers, see: (a) Vauzeilles, B.; Cravo, D.; Mallet, J.-M.; Sinaÿ, P. Synlett 1993, 552. Xin, Y. C.; Mallet, J.-M.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1993, 864. Mallet, A.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1994, 5, 2593. Chénedé, A.; Perrin, E.; Rekaï, E. D.; Sinaÿ, P. Synlett 1994, 420. (b) Johnson, C. R.; Miller, M. W.; Golebiowski, A.; Sundram, H.; Ksebati, M. B. Tetrahedron Lett. 1994, 35, 8991. (c) Ferritto, R.; Vogel, P. Tetrahedron: Asymmetry 1994, 5, 2077. (d) Paton, R. M.; Penman, K. J. Tetrahedron Lett. 1994, 35, 3163. (e) Armstrong, R. W.; Sutherlin, D. P. Tetrahedron Lett. 1994, 35, 7743. (f) Lay, L. Nicotra, F.; Pangrazio, C.; Panza, L.; Russo, G. J. Chem. Soc., Perkin Trans. 1 1994, 333. (g) Dietrich, H.; Schmidt, R. R. Liebigs Ann. Chem. 1994, 975. (h) Mazéas, D.; Skrydstrup, T.; Doumeix, O.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1383. Mazéas, D.; Skrydstrup, T.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1995, 34, 909. (i) Eyrisch, O.; Fessner, W.-D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1639. (j) Sutherlin, D. P.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 9802. (k) Wong, C.-H.; Hung, S.-C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2671. (l) Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. J. 1996, 2, 502. (m) Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894. (n) Dondoni, A.; Boscarato, A.; Zuurmond, H.-M. Tetrahedron Lett. 1996, 37, 7587. (o) Martin, O. R.; Liu, L.; Yang, F. Tetrahedron Lett. 1996, 37, 1991. (p) Baudat, A.; Vogel, P. Tetrahedron Lett. 1996, 37, 483. (q) Vlahov, I. R.; Vlahova, P. I.; Linhardt, R. J. J. Am. Chem. Soc. 1997, 119, 1480. (r) Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215. (s) Dondoni, A.; Kniezo, L.; Martinkova, M.; Imrich, J. Chem. Eur. J. 1997, 3, 424.
43. For selected recent papers, see: (a) Vauzeilles, B.; Cravo, D.; Mallet, J.-M.; Sinaÿ, P. Synlett 1993, 552. Xin, Y. C.; Mallet, J.-M.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1993, 864. Mallet, A.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1994, 5, 2593. Chénedé, A.; Perrin, E.; Rekaï, E. D.; Sinaÿ, P. Synlett 1994, 420. (b) Johnson, C. R.; Miller, M. W.; Golebiowski, A.; Sundram, H.; Ksebati, M. B. Tetrahedron Lett. 1994, 35, 8991. (c) Ferritto, R.; Vogel, P. Tetrahedron: Asymmetry 1994, 5, 2077. (d) Paton, R. M.; Penman, K. J. Tetrahedron Lett. 1994, 35, 3163. (e) Armstrong, R. W.; Sutherlin, D. P. Tetrahedron Lett. 1994, 35, 7743. (f) Lay, L. Nicotra, F.; Pangrazio, C.; Panza, L.; Russo, G. J. Chem. Soc., Perkin Trans. 1 1994, 333. (g) Dietrich, H.; Schmidt, R. R. Liebigs Ann. Chem. 1994, 975. (h) Mazéas, D.; Skrydstrup, T.; Doumeix, O.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1383. Mazéas, D.; Skrydstrup, T.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1995, 34, 909. (i) Eyrisch, O.; Fessner, W.-D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1639. (j) Sutherlin, D. P.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 9802. (k) Wong, C.-H.; Hung, S.-C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2671. (l) Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. J. 1996, 2, 502. (m) Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894. (n) Dondoni, A.; Boscarato, A.; Zuurmond, H.-M. Tetrahedron Lett. 1996, 37, 7587. (o) Martin, O. R.; Liu, L.; Yang, F. Tetrahedron Lett. 1996, 37, 1991. (p) Baudat, A.; Vogel, P. Tetrahedron Lett. 1996, 37, 483. (q) Vlahov, I. R.; Vlahova, P. I.; Linhardt, R. J. J. Am. Chem. Soc. 1997, 119, 1480. (r) Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215. (s) Dondoni, A.; Kniezo, L.; Martinkova, M.; Imrich, J. Chem. Eur. J. 1997, 3, 424.
44. For selected recent papers, see: (a) Vauzeilles, B.; Cravo, D.; Mallet, J.-M.; Sinaÿ, P. Synlett 1993, 552. Xin, Y. C.; Mallet, J.-M.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1993, 864. Mallet, A.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1994, 5, 2593. Chénedé, A.; Perrin, E.; Rekaï, E. D.; Sinaÿ, P. Synlett 1994, 420. (b) Johnson, C. R.; Miller, M. W.; Golebiowski, A.; Sundram, H.; Ksebati, M. B. Tetrahedron Lett. 1994, 35, 8991. (c) Ferritto, R.; Vogel, P. Tetrahedron: Asymmetry 1994, 5, 2077. (d) Paton, R. M.; Penman, K. J. Tetrahedron Lett. 1994, 35, 3163. (e) Armstrong, R. W.; Sutherlin, D. P. Tetrahedron Lett. 1994, 35, 7743. (f) Lay, L. Nicotra, F.; Pangrazio, C.; Panza, L.; Russo, G. J. Chem. Soc., Perkin Trans. 1 1994, 333. (g) Dietrich, H.; Schmidt, R. R. Liebigs Ann. Chem. 1994, 975. (h) Mazéas, D.; Skrydstrup, T.; Doumeix, O.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1383. Mazéas, D.; Skrydstrup, T.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1995, 34, 909. (i) Eyrisch, O.; Fessner, W.-D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1639. (j) Sutherlin, D. P.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 9802. (k) Wong, C.-H.; Hung, S.-C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2671. (l) Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. J. 1996, 2, 502. (m) Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894. (n) Dondoni, A.; Boscarato, A.; Zuurmond, H.-M. Tetrahedron Lett. 1996, 37, 7587. (o) Martin, O. R.; Liu, L.; Yang, F. Tetrahedron Lett. 1996, 37, 1991. (p) Baudat, A.; Vogel, P. Tetrahedron Lett. 1996, 37, 483. (q) Vlahov, I. R.; Vlahova, P. I.; Linhardt, R. J. J. Am. Chem. Soc. 1997, 119, 1480. (r) Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215. (s) Dondoni, A.; Kniezo, L.; Martinkova, M.; Imrich, J. Chem. Eur. J. 1997, 3, 424.
45. For selected recent papers, see: (a) Vauzeilles, B.; Cravo, D.; Mallet, J.-M.; Sinaÿ, P. Synlett 1993, 552. Xin, Y. C.; Mallet, J.-M.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1993, 864. Mallet, A.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1994, 5, 2593. Chénedé, A.; Perrin, E.; Rekaï, E. D.; Sinaÿ, P. Synlett 1994, 420. (b) Johnson, C. R.; Miller, M. W.; Golebiowski, A.; Sundram, H.; Ksebati, M. B. Tetrahedron Lett. 1994, 35, 8991. (c) Ferritto, R.; Vogel, P. Tetrahedron: Asymmetry 1994, 5, 2077. (d) Paton, R. M.; Penman, K. J. Tetrahedron Lett. 1994, 35, 3163. (e) Armstrong, R. W.; Sutherlin, D. P. Tetrahedron Lett. 1994, 35, 7743. (f) Lay, L. Nicotra, F.; Pangrazio, C.; Panza, L.; Russo, G. J. Chem. Soc., Perkin Trans. 1 1994, 333. (g) Dietrich, H.; Schmidt, R. R. Liebigs Ann. Chem. 1994, 975. (h) Mazéas, D.; Skrydstrup, T.; Doumeix, O.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1383. Mazéas, D.; Skrydstrup, T.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1995, 34, 909. (i) Eyrisch, O.; Fessner, W.-D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1639. (j) Sutherlin, D. P.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 9802. (k) Wong, C.-H.; Hung, S.-C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2671. (l) Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. J. 1996, 2, 502. (m) Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894. (n) Dondoni, A.; Boscarato, A.; Zuurmond, H.-M. Tetrahedron Lett. 1996, 37, 7587. (o) Martin, O. R.; Liu, L.; Yang, F. Tetrahedron Lett. 1996, 37, 1991. (p) Baudat, A.; Vogel, P. Tetrahedron Lett. 1996, 37, 483. (q) Vlahov, I. R.; Vlahova, P. I.; Linhardt, R. J. J. Am. Chem. Soc. 1997, 119, 1480. (r) Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215. (s) Dondoni, A.; Kniezo, L.; Martinkova, M.; Imrich, J. Chem. Eur. J. 1997, 3, 424.
46. For selected recent papers, see: (a) Vauzeilles, B.; Cravo, D.; Mallet, J.-M.; Sinaÿ, P. Synlett 1993, 552. Xin, Y. C.; Mallet, J.-M.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1993, 864. Mallet, A.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1994, 5, 2593. Chénedé, A.; Perrin, E.; Rekaï, E. D.; Sinaÿ, P. Synlett 1994, 420. (b) Johnson, C. R.; Miller, M. W.; Golebiowski, A.; Sundram, H.; Ksebati, M. B. Tetrahedron Lett. 1994, 35, 8991. (c) Ferritto, R.; Vogel, P. Tetrahedron: Asymmetry 1994, 5, 2077. (d) Paton, R. M.; Penman, K. J. Tetrahedron Lett. 1994, 35, 3163. (e) Armstrong, R. W.; Sutherlin, D. P. Tetrahedron Lett. 1994, 35, 7743. (f) Lay, L. Nicotra, F.; Pangrazio, C.; Panza, L.; Russo, G. J. Chem. Soc., Perkin Trans. 1 1994, 333. (g) Dietrich, H.; Schmidt, R. R. Liebigs Ann. Chem. 1994, 975. (h) Mazéas, D.; Skrydstrup, T.; Doumeix, O.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1383. Mazéas, D.; Skrydstrup, T.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1995, 34, 909. (i) Eyrisch, O.; Fessner, W.-D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1639. (j) Sutherlin, D. P.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 9802. (k) Wong, C.-H.; Hung, S.-C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2671. (l) Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. J. 1996, 2, 502. (m) Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894. (n) Dondoni, A.; Boscarato, A.; Zuurmond, H.-M. Tetrahedron Lett. 1996, 37, 7587. (o) Martin, O. R.; Liu, L.; Yang, F. Tetrahedron Lett. 1996, 37, 1991. (p) Baudat, A.; Vogel, P. Tetrahedron Lett. 1996, 37, 483. (q) Vlahov, I. R.; Vlahova, P. I.; Linhardt, R. J. J. Am. Chem. Soc. 1997, 119, 1480. (r) Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215. (s) Dondoni, A.; Kniezo, L.; Martinkova, M.; Imrich, J. Chem. Eur. J. 1997, 3, 424.
47. For selected recent papers, see: (a) Vauzeilles, B.; Cravo, D.; Mallet, J.-M.; Sinaÿ, P. Synlett 1993, 552. Xin, Y. C.; Mallet, J.-M.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1993, 864. Mallet, A.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1994, 5, 2593. Chénedé, A.; Perrin, E.; Rekaï, E. D.; Sinaÿ, P. Synlett 1994, 420. (b) Johnson, C. R.; Miller, M. W.; Golebiowski, A.; Sundram, H.; Ksebati, M. B. Tetrahedron
48. For selected recent papers, see: (a) Vauzeilles, B.; Cravo, D.; Mallet, J.-M.; Sinaÿ, P. Synlett 1993, 552. Xin, Y. C.; Mallet, J.-M.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1993, 864. Mallet, A.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1994, 5, 2593. Chénedé, A.; Perrin, E.; Rekaï, E. D.; Sinaÿ, P. Synlett 1994, 420. (b) Johnson, C. R.; Miller, M. W.; Golebiowski, A.; Sundram, H.; Ksebati, M. B. Tetrahedron Lett. 1994, 35, 8991. (c) Ferritto, R.; Vogel, P. Tetrahedron: Asymmetry 1994, 5, 2077. (d) Paton, R. M.; Penman, K. J. Tetrahedron Lett. 1994, 35, 3163. (e) Armstrong, R. W.; Sutherlin, D. P. Tetrahedron Lett. 1994, 35, 7743. (f) Lay, L. Nicotra, F.; Pangrazio, C.; Panza, L.; Russo, G. J. Chem. Soc., Perkin Trans. 1 1994, 333. (g) Dietrich, H.; Schmidt, R. R. Liebigs Ann. Chem. 1994, 975. (h) Mazéas, D.; Skrydstrup, T.; Doumeix, O.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1383. Mazéas, D.; Skrydstrup, T.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1995, 34, 909. (i) Eyrisch, O.; Fessner, W.-D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1639. (j) Sutherlin, D. P.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 9802. (k) Wong, C.-H.; Hung, S.-C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2671. (l) Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. J. 1996, 2, 502. (m) Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894. (n) Dondoni, A.; Boscarato, A.; Zuurmond, H.-M. Tetrahedron Lett. 1996, 37, 7587. (o) Martin, O. R.; Liu, L.; Yang, F. Tetrahedron Lett. 1996, 37, 1991. (p) Baudat, A.; Vogel, P. Tetrahedron Lett. 1996, 37, 483. (q) Vlahov, I. R.; Vlahova, P. I.; Linhardt, R. J. J. Am. Chem. Soc. 1997, 119, 1480. (r) Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215. (s) Dondoni, A.; Kniezo, L.; Martinkova, M.; Imrich, J. Chem. Eur. J. 1997, 3, 424.
49. For selected recent papers, see: (a) Vauzeilles, B.; Cravo, D.; Mallet, J.-M.; Sinaÿ, P. Synlett 1993, 552. Xin, Y. C.; Mallet, J.-M.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1993, 864. Mallet, A.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1994, 5, 2593. Chénedé, A.; Perrin, E.; Rekaï, E. D.; Sinaÿ, P. Synlett 1994, 420. (b) Johnson, C. R.; Miller, M. W.; Golebiowski, A.; Sundram, H.; Ksebati, M. B. Tetrahedron Lett. 1994, 35, 8991. (c) Ferritto, R.; Vogel, P. Tetrahedron: Asymmetry 1994, 5, 2077. (d) Paton, R. M.; Penman, K. J. Tetrahedron Lett. 1994, 35, 3163. (e) Armstrong, R. W.; Sutherlin, D. P. Tetrahedron Lett. 1994, 35, 7743. (f) Lay, L. Nicotra, F.; Pangrazio, C.; Panza, L.; Russo, G. J. Chem. Soc., Perkin Trans. 1 1994, 333. (g) Dietrich, H.; Schmidt, R. R. Liebigs Ann. Chem. 1994, 975. (h) Mazéas, D.; Skrydstrup, T.; Doumeix, O.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1383. Mazéas, D.; Skrydstrup, T.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1995, 34, 909. (i) Eyrisch, O.; Fessner, W.-D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1639. (j) Sutherlin, D. P.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 9802. (k) Wong, C.-H.; Hung, S.-C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2671. (l) Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. J. 1996, 2, 502. (m) Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894. (n) Dondoni, A.; Boscarato, A.; Zuurmond, H.-M. Tetrahedron Lett. 1996, 37, 7587. (o) Martin, O. R.; Liu, L.; Yang, F. Tetrahedron Lett. 1996, 37, 1991. (p) Baudat, A.; Vogel, P. Tetrahedron Lett. 1996, 37, 483. (q) Vlahov, I. R.; Vlahova, P. I.; Linhardt, R. J. J. Am. Chem. Soc. 1997, 119, 1480. (r) Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215. (s) Dondoni, A.; Kniezo, L.; Martinkova, M.; Imrich, J. Chem. Eur. J. 1997, 3, 424.
50. For selected recent papers, see: (a) Vauzeilles, B.; Cravo, D.; Mallet, J.-M.; Sinaÿ, P. Synlett 1993, 552. Xin, Y. C.; Mallet, J.-M.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1993, 864. Mallet, A.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1994, 5, 2593. Chénedé, A.; Perrin, E.; Rekaï, E. D.; Sinaÿ, P. Synlett 1994, 420. (b) Johnson, C. R.; Miller, M. W.; Golebiowski, A.; Sundram, H.; Ksebati, M. B. Tetrahedron Lett. 1994, 35, 8991. (c) Ferritto, R.; Vogel, P. Tetrahedron: Asymmetry 1994, 5, 2077. (d) Paton, R. M.; Penman, K. J. Tetrahedron Lett. 1994, 35, 3163. (e) Armstrong, R. W.; Sutherlin, D. P. Tetrahedron Lett. 1994, 35, 7743. (f) Lay, L. Nicotra, F.; Pangrazio, C.; Panza, L.; Russo, G. J. Chem. Soc., Perkin Trans. 1 1994, 333. (g) Dietrich, H.; Schmidt, R. R. Liebigs Ann. Chem. 1994, 975. (h) Mazéas, D.; Skrydstrup, T.; Doumeix, O.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1994, 33, 1383. Mazéas, D.; Skrydstrup, T.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1995, 34, 909. (i) Eyrisch, O.; Fessner, W.-D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1639. (j) Sutherlin, D. P.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 9802. (k) Wong, C.-H.; Hung, S.-C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2671. (l) Streicher, H.; Geyer, A.; Schmidt, R. R. Chem. Eur. J. 1996, 2, 502. (m) Kobertz, W. R.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894. (n) Dondoni, A.; Boscarato, A.; Zuurmond, H.-M. Tetrahedron Lett. 1996, 37, 7587. (o) Martin, O. R.; Liu, L.; Yang, F. Tetrahedron Lett. 1996, 37, 1991. (p) Baudat, A.; Vogel, P. Tetrahedron Lett. 1996, 37, 483. (q) Vlahov, I. R.; Vlahova, P. I.; Linhardt, R. J. J. Am. Chem. Soc. 1997, 119, 1480. (r) Witczak, Z. J.; Chhabra, R.; Chojnacki, J. Tetrahedron Lett. 1997, 38, 2215. (s) Dondoni, A.; Kniezo, L.; Martinkova, M.; Imrich, J. Chem. Eur. J. 1997, 3, 424.
51. (a) For general information, see: Lagerie, P.; Legler, G.; Yon, D. M. Biochemie 1982, 64, 977. Truscheit, E.; Frommer, W.; Junge, B.; Müller, L.; Schmid, D. D.; Wingender, W. Angew. Chem., Int. Ed. Engl. 1981, 20, 744. Sinnott, M. L. In Enzyme Mechanisms; Page, M. I., Williams, A., Eds.; The Royal Society of Chemistry: London, 1987; p 259.
52. (a) For general information, see: Lagerie, P.; Legler, G.; Yon, D. M. Biochemie 1982, 64, 977. Truscheit, E.; Frommer, W.; Junge, B.; Müller, L.; Schmid, D. D.; Wingender, W. Angew. Chem., Int. Ed. Engl. 1981, 20, 744. Sinnott, M. L. In Enzyme Mechanisms; Page, M. I., Williams, A., Eds.; The Royal Society of Chemistry: London, 1987; p 259.
53. (a) For general information, see: Lagerie, P.; Legler, G.; Yon, D. M. Biochemie 1982, 64, 977. Truscheit, E.; Frommer, W.; Junge, B.; Müller, L.; Schmid, D. D.; Wingender, W. Angew. Chem., Int. Ed. Engl. 1981, 20, 744. Sinnott, M. L. In Enzyme Mechanisms; Page, M. I., Williams, A., Eds.; The Royal Society of Chemistry: London, 1987; p 259.
54. (b) For some applications, see: Treatment of AIDS (Karpas, A.; Fleet, G. W. J.; Dwek, R. A.; Fellows, L. E.; Tyms, A. S.; Petursson, S.; Namgoong, S. K.; Ramsden, N. G.; Jacob, G. S.; Rademacher, T. W. Proc. Nat. Acad. Sci. U.S.A. 1988, 85, 9229); treatment of diabetes (Robinson, K. M.; Becovic, M. E.; Rhinehart, B. L.; Heineke, E. W.; Ducep, J.-B.; Kastner, P. R.; Marshall, F. N.; Danzin, C. Diabetes 1991, 40, 825); tumor metastasis (Bernacki, R. J.; Niedbala, M. J.; Korytnyk, W. Cancer Metastasis Rev. 1985, 4, 81).
55. (b) For some applications, see: Treatment of AIDS (Karpas, A.; Fleet, G. W. J.; Dwek, R. A.; Fellows, L. E.; Tyms, A. S.; Petursson, S.; Namgoong, S. K.; Ramsden, N. G.; Jacob, G. S.; Rademacher, T. W. Proc. Nat. Acad. Sci. U.S.A. 1988, 85, 9229); treatment of diabetes (Robinson, K. M.; Becovic, M. E.; Rhinehart, B. L.; Heineke, E. W.; Ducep, J.-B.; Kastner, P. R.; Marshall, F. N.; Danzin, C. Diabetes 1991, 40, 825); tumor metastasis (Bernacki, R. J.; Niedbala, M. J.; Korytnyk, W. Cancer Metastasis Rev. 1985, 4, 81).
56. (b) For some applications, see: Treatment of AIDS (Karpas, A.; Fleet, G. W. J.; Dwek, R. A.; Fellows, L. E.; Tyms, A. S.; Petursson, S.; Namgoong, S. K.; Ramsden, N. G.; Jacob, G. S.; Rademacher, T. W. Proc. Nat. Acad. Sci. U.S.A. 1988, 85, 9229); treatment of diabetes (Robinson, K. M.; Becovic, M. E.; Rhinehart, B. L.; Heineke, E. W.; Ducep, J.-B.; Kastner, P. R.; Marshall, F. N.; Danzin, C. Diabetes 1991, 40, 825); tumor metastasis (Bernacki, R. J.; Niedbala, M. J.; Korytnyk, W. Cancer Metastasis Rev. 1985, 4, 81).
57. Rademacher, T. W.; Parekh, R. B.; Dwek, R. A. Annu. Rev. Biochem. 1988, 57, 785. Hindsgaul, O.; Kare, D. P.; Bach, M.; Lemieux, R. U. Can. J. Chem. 1985, 63, 2653. Feizi, T. In Carbohydate Recognition in Cellular Function; Ciba-Geigy Symposium 145; Wiley: Chichester, 1989; p 62. Kornfeld, R.; Kornfeld, S. Annu. Rev. Biochem. 1985, 54, 651 and references therein. Morenem, K. W.; Trimble, R. B.; Herscovics, A. Glycobiology 1994, 4, 113.
58. Rademacher, T. W.; Parekh, R. B.; Dwek, R. A. Annu. Rev. Biochem. 1988, 57, 785. Hindsgaul, O.; Kare, D. P.; Bach, M.; Lemieux, R. U. Can. J. Chem. 1985, 63, 2653. Feizi, T. In Carbohydate Recognition in Cellular Function; Ciba-Geigy Symposium 145; Wiley: Chichester, 1989; p 62. Kornfeld, R.; Kornfeld, S. Annu. Rev. Biochem. 1985, 54, 651 and references therein. Morenem, K. W.; Trimble, R. B.; Herscovics, A. Glycobiology 1994, 4, 113.
59. Rademacher, T. W.; Parekh, R. B.; Dwek, R. A. Annu. Rev. Biochem. 1988, 57, 785. Hindsgaul, O.; Kare, D. P.; Bach, M.; Lemieux, R. U. Can. J. Chem. 1985, 63, 2653. Feizi, T. In Carbohydate Recognition in Cellular Function; Ciba-Geigy Symposium 145; Wiley: Chichester, 1989; p 62. Kornfeld, R.; Kornfeld, S. Annu. Rev. Biochem. 1985, 54, 651 and references therein. Morenem, K. W.; Trimble, R. B.; Herscovics, A. Glycobiology 1994, 4, 113.
60. Rademacher, T. W.; Parekh, R. B.; Dwek, R. A. Annu. Rev. Biochem. 1988, 57, 785. Hindsgaul, O.; Kare, D. P.; Bach, M.; Lemieux, R. U. Can. J. Chem. 1985, 63, 2653. Feizi, T. In Carbohydate Recognition in Cellular Function; Ciba-Geigy Symposium 145; Wiley: Chichester, 1989; p 62. Kornfeld, R.; Kornfeld, S. Annu. Rev. Biochem. 1985, 54, 651 and references therein. Morenem, K. W.; Trimble, R. B.; Herscovics, A. Glycobiology 1994, 4, 113.
61. Rademacher, T. W.; Parekh, R. B.; Dwek, R. A. Annu. Rev. Biochem. 1988, 57, 785. Hindsgaul, O.; Kare, D. P.; Bach, M.; Lemieux, R. U. Can. J. Chem. 1985, 63, 2653. Feizi, T. In Carbohydate Recognition in Cellular Function; Ciba-Geigy Symposium 145; Wiley: Chichester, 1989; p 62. Kornfeld, R.; Kornfeld, S. Annu. Rev. Biochem. 1985, 54, 651 and references therein. Morenem, K. W.; Trimble, R. B.; Herscovics, A. Glycobiology 1994, 4, 113.
62. O'Leary, D. J.; Kishi, Y. J. Org. Chem. 1994, 59, 6629. Wei, A.; Haudrechy, A.; Audin, C.; Jun, H.-S.; Haudrechy-Bretel, N.; Kishi, Y. J. Org. Chem. 1995, 60, 2160. Wei, A.; Boy, K. M.; Kishi, Y. J. Am. Chem. Soc. 1995, 117, 9432 and previous papers. Espinosa, J.-F.; Canada, F. J.; Asensio, J. L.; Dietrich, H.; Martín-Lomas, M.; Schmidt, R. R.; Jiménez-Barbero, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 303.
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64. O'Leary, D. J.; Kishi, Y. J. Org. Chem. 1994, 59, 6629. Wei, A.; Haudrechy, A.; Audin, C.; Jun, H.-S.; Haudrechy-Bretel, N.; Kishi, Y. J. Org. Chem. 1995, 60, 2160. Wei, A.; Boy, K. M.; Kishi, Y. J. Am. Chem. Soc. 1995, 117, 9432 and previous papers. Espinosa, J.-F.; Canada, F. J.; Asensio, J. L.; Dietrich, H.; Martín-Lomas, M.; Schmidt, R. R.; Jiménez-Barbero, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 303.
65. O'Leary, D. J.; Kishi, Y. J. Org. Chem. 1994, 59, 6629. Wei, A.; Haudrechy, A.; Audin, C.; Jun, H.-S.; Haudrechy-Bretel, N.; Kishi, Y. J. Org. Chem. 1995, 60, 2160. Wei, A.; Boy, K. M.; Kishi, Y. J. Am. Chem. Soc. 1995, 117, 9432 and previous papers. Espinosa, J.-F.; Canada, F. J.; Asensio, J. L.; Dietrich, H.; Martín-Lomas, M.; Schmidt, R. R.; Jiménez-Barbero, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 303.
66. The "stereocontrolled synthesis of disaccharides via the temporary silicon connection" was originally described by Stork, G.; Suh, H. S.; Kim, G. J. Am. Chem. Soc. 1991, 113, 7054.
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73. For instance, the aldehyde 1 is currently prepared in our laboratory in stocks of 5.5-6.0 g (ca. 65% yield) starting from 9.0 g of the tetrabenzyl galactonolactone.
74. Secrist, J. A., III; Wu, S.-R. J. Org. Chem. 1979, 44, 1434.
75. (a) Secrist, J. A., III; Wu, S.-R. J. Org. Chem. 1977, 42, 4084.
76. (b) For an authorative review on the stereochemistry, mechanism, and synthetic applications of the Wittig olefination, see: Maryanoff, B. E.; Reitz, A. B. Chem. Rev. (Washington, D.C.) 1989, 89, 863.
77. Sakairi, N.; Kuzuhara, H. Tetrahedron Lett. 1982, 23, 5327.
78. 3 at room temperature. However, a filtration over a short column of silica gel just prior to use gave pure products showing simple NMR spectra.
79. (a) Warren, S.; Clayden, J. Angew. Chem., Int. Ed. Engl. 1996, 35, 241.
80. (b) Smith, D. J. H. In Comprehensive Organic Chemistry; Barton, D., Ollis, W. D., Eds.; Pergamon Press Ltd: Oxford, 1979; p 1301.
81. 6,7 values (11-12 Hz) were in the range of cis ethylenic coupling constants. See: Jackman, L. M.; Sternhell, S. In Applications of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry; Barton, D., Ed.; Pergamon Press Ltd: Oxford, 1969; p 301. Silverstein, R. M.; Bassler, G. C.; Morrill, T. C. In Spectrometric Identification of Organic Compounds; John Wiley & Sons, Inc.: New York, 1991; p 221.
82. 6,7 values (11-12 Hz) were in the range of cis ethylenic coupling constants. See: Jackman, L. M.; Sternhell, S. In Applications of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry; Barton, D., Ed.; Pergamon Press Ltd: Oxford, 1969; p 301. Silverstein, R. M.; Bassler, G. C.; Morrill, T. C. In Spectrometric Identification of Organic Compounds; John Wiley & Sons, Inc.: New York, 1991; p 221.
83. 4,5 value of 2.0 Hz.
84. For all sugar olefins and the corresponding alkanes the same conventional numbering system outlined for 10 and 18 was adopted; i.e., counting starts from the reducing end of the disaccharide.
85. Paulsen, H.; Hölck, J.-P. Carbohydr. Res. 1982, 109, 89.
86. Dondoni, A.; Perrone, D.; Semola, M. T. J. Org. Chem. 1995, 60, 7927.
87. Brown, H. C.; Brown, C. A. J. Am. Chem. Soc. 1963, 85, 1003.
88. Rouzaud, D.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1983, 1353.
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91. Hoffmann, M.; Kessler, H. Tetrahedron Lett. 1994, 35, 6067.
92. Ayadi, E.; Czernecki, S.; Xie, J. Chem. Commun. 1996, 347. The key reaction in this paper is the addition of alkyllithium reagents to 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-galactonolactone. It is worth pointing out that the original synthesis of the azido sugar lactone and its reaction with a C-nucleophile (2-lithiothiazole) described by one of us in a much earlier report (ref 12) were not acknowledged.
93. Ohrui, H.; Jones, G. H.; Moffatt, J. G.; Maddox, M. L.; Christensen, A. T.; Byram, S. K. J. Am. Chem. Soc. 1975, 97, 4602.
94. 3OD) δ 22.8, 24.5, 25.1, 26.3, 31.3, 33.2, 64.6, 68.7, 71.9, 72.3, 73.9, 74.0, 74.4, 76.0, 98.0, 109.6, 110.0.
95. van Tamelen, E. E.; Dewey, R. S. J. Am. Chem. Soc. 1961, 83, 3729.
96. 3SiH-TMSOTf (ref 12).
97. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals, 3rd ed.; Pergamon Press: Oxford, 1988.
98. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.