Stereoselective Synthesis of α-C-Galactopyranosides of Conduritols and Aminoconduritols

Synlett

Volumn 1996, Issue 3, 1996, Pages 281-282

  Ferritto, Rafael ^a   Vogel, Pierre ^a  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001255912     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5372     Document Type: Article

References (41)

1. See e.g.: Karlsson, K. A. Annu. Rev. Biochem. 1989, 58, 309; Sharon, N.; Lis, H. Science 1989, 246, 227; Lasky, L. A. Science 1992, 258, 964; Sharon, N.; Lis, H. Sci. Am. 1993, 268, 82; Feizi, T. Curr. Opin. Struct. Biol. 1993, 3, 701; Varki, A. Proc. Natl. Acad. Sci. USA 1994, 91, 7390.
2. See e.g.: Karlsson, K. A. Annu. Rev. Biochem. 1989, 58, 309; Sharon, N.; Lis, H. Science 1989, 246, 227; Lasky, L. A. Science 1992, 258, 964; Sharon, N.; Lis, H. Sci. Am. 1993, 268, 82; Feizi, T. Curr. Opin. Struct. Biol. 1993, 3, 701; Varki, A. Proc. Natl. Acad. Sci. USA 1994, 91, 7390.
3. See e.g.: Karlsson, K. A. Annu. Rev. Biochem. 1989, 58, 309; Sharon, N.; Lis, H. Science 1989, 246, 227; Lasky, L. A. Science 1992, 258, 964; Sharon, N.; Lis, H. Sci. Am. 1993, 268, 82; Feizi, T. Curr. Opin. Struct. Biol. 1993, 3, 701; Varki, A. Proc. Natl. Acad. Sci. USA 1994, 91, 7390.
4. See e.g.: Karlsson, K. A. Annu. Rev. Biochem. 1989, 58, 309; Sharon, N.; Lis, H. Science 1989, 246, 227; Lasky, L. A. Science 1992, 258, 964; Sharon, N.; Lis, H. Sci. Am. 1993, 268, 82; Feizi, T. Curr. Opin. Struct. Biol. 1993, 3, 701; Varki, A. Proc. Natl. Acad. Sci. USA 1994, 91, 7390.
5. See e.g.: Karlsson, K. A. Annu. Rev. Biochem. 1989, 58, 309; Sharon, N.; Lis, H. Science 1989, 246, 227; Lasky, L. A. Science 1992, 258, 964; Sharon, N.; Lis, H. Sci. Am. 1993, 268, 82; Feizi, T. Curr. Opin. Struct. Biol. 1993, 3, 701; Varki, A. Proc. Natl. Acad. Sci. USA 1994, 91, 7390.
6. See e.g.: Karlsson, K. A. Annu. Rev. Biochem. 1989, 58, 309; Sharon, N.; Lis, H. Science 1989, 246, 227; Lasky, L. A. Science 1992, 258, 964; Sharon, N.; Lis, H. Sci. Am. 1993, 268, 82; Feizi, T. Curr. Opin. Struct. Biol. 1993, 3, 701; Varki, A. Proc. Natl. Acad. Sci. USA 1994, 91, 7390.
7. See e.g., Aebischer, B.; Bieri, J. H.; Prewo, R.; Vasella, A. Helv. Chim. Acta 1982, 65, 2251; Rouzaud, D.; Sinay, P. J. Chem. Soc., Chem. Commun. 1983, 1353; Giese, B.; Witzel, T. Angew. Chem., Int. Ed. Engl. 1986, 25, 450; Babirad, S. A.; Wang, Y.; Kishi, Y. J. Org. Chem. 1987, 52, 1370; Bimwala, R. M.; Vogel, P. J. Org. Chem. 1992, 57, 2076; Dietrich, H.; Schmidt, R. R. Liebigs Ann. Chem. 1994, 975; Mallet, A.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron Asymm. 1994, 5, 2593; Paton, R. M.; Penman, K. J. Tetrahedron Lett. 1994, 35, 3163; Mazéas, D.; Skrydstrup, T.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1995, 34, 909; Eyrisch, O.; Fessner, W.-D. Ibid. 1995, 34, 1639; Sarabia-Garcia, F.; López-Herrera, F. J.; Pino González, M. S. Tetrahedron 1995, 51, 5491 and references cited in these papers.
8. See e.g., Aebischer, B.; Bieri, J. H.; Prewo, R.; Vasella, A. Helv. Chim. Acta 1982, 65, 2251; Rouzaud, D.; Sinay, P. J. Chem. Soc., Chem. Commun. 1983, 1353; Giese, B.; Witzel, T. Angew. Chem., Int. Ed. Engl. 1986, 25, 450; Babirad, S. A.; Wang, Y.; Kishi, Y. J. Org. Chem. 1987, 52, 1370; Bimwala, R. M.; Vogel, P. J. Org. Chem. 1992, 57, 2076; Dietrich, H.; Schmidt, R. R. Liebigs Ann. Chem. 1994, 975; Mallet, A.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron Asymm. 1994, 5, 2593; Paton, R. M.; Penman, K. J. Tetrahedron Lett. 1994, 35, 3163; Mazéas, D.; Skrydstrup, T.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1995, 34, 909; Eyrisch, O.; Fessner, W.-D. Ibid. 1995, 34, 1639; Sarabia-Garcia, F.; López-Herrera, F. J.; Pino González, M. S. Tetrahedron 1995, 51, 5491 and references cited in these papers.
9. See e.g., Aebischer, B.; Bieri, J. H.; Prewo, R.; Vasella, A. Helv. Chim. Acta 1982, 65, 2251; Rouzaud, D.; Sinay, P. J. Chem. Soc., Chem. Commun. 1983, 1353; Giese, B.; Witzel, T. Angew. Chem., Int. Ed. Engl. 1986, 25, 450; Babirad, S. A.; Wang, Y.; Kishi, Y. J. Org. Chem. 1987, 52, 1370; Bimwala, R. M.; Vogel, P. J. Org. Chem. 1992, 57, 2076; Dietrich, H.; Schmidt, R. R. Liebigs Ann. Chem. 1994, 975; Mallet, A.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron Asymm. 1994, 5, 2593; Paton, R. M.; Penman, K. J. Tetrahedron Lett. 1994, 35, 3163; Mazéas, D.; Skrydstrup, T.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1995, 34, 909; Eyrisch, O.; Fessner, W.-D. Ibid. 1995, 34, 1639; Sarabia-Garcia, F.; López-Herrera, F. J.; Pino González, M. S. Tetrahedron 1995, 51, 5491 and references cited in these papers.
10. See e.g., Aebischer, B.; Bieri, J. H.; Prewo, R.; Vasella, A. Helv. Chim. Acta 1982, 65, 2251; Rouzaud, D.; Sinay, P. J. Chem. Soc., Chem. Commun. 1983, 1353; Giese, B.; Witzel, T. Angew. Chem., Int. Ed. Engl. 1986, 25, 450; Babirad, S. A.; Wang, Y.; Kishi, Y. J. Org. Chem. 1987, 52, 1370; Bimwala, R. M.; Vogel, P. J. Org. Chem. 1992, 57, 2076; Dietrich, H.; Schmidt, R. R. Liebigs Ann. Chem. 1994, 975; Mallet, A.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron Asymm. 1994, 5, 2593; Paton, R. M.; Penman, K. J. Tetrahedron Lett. 1994, 35, 3163; Mazéas, D.; Skrydstrup, T.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1995, 34, 909; Eyrisch, O.; Fessner, W.-D. Ibid. 1995, 34, 1639; Sarabia-Garcia, F.; López-Herrera, F. J.; Pino González, M. S. Tetrahedron 1995, 51, 5491 and references cited in these papers.
11. See e.g., Aebischer, B.; Bieri, J. H.; Prewo, R.; Vasella, A. Helv. Chim. Acta 1982, 65, 2251; Rouzaud, D.; Sinay, P. J. Chem. Soc., Chem. Commun. 1983, 1353; Giese, B.; Witzel, T. Angew. Chem., Int. Ed. Engl. 1986, 25, 450; Babirad, S. A.; Wang, Y.; Kishi, Y. J. Org. Chem. 1987, 52, 1370; Bimwala, R. M.; Vogel, P. J. Org. Chem. 1992, 57, 2076; Dietrich, H.; Schmidt, R. R. Liebigs Ann. Chem. 1994, 975; Mallet, A.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron Asymm. 1994, 5, 2593; Paton, R. M.; Penman, K. J. Tetrahedron Lett. 1994, 35, 3163; Mazéas, D.; Skrydstrup, T.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1995, 34, 909; Eyrisch, O.; Fessner, W.-D. Ibid. 1995, 34, 1639; Sarabia-Garcia, F.; López-Herrera, F. J.; Pino González, M. S. Tetrahedron 1995, 51, 5491 and references cited in these papers.
12. See e.g., Aebischer, B.; Bieri, J. H.; Prewo, R.; Vasella, A. Helv. Chim. Acta 1982, 65, 2251; Rouzaud, D.; Sinay, P. J. Chem. Soc., Chem. Commun. 1983, 1353; Giese, B.; Witzel, T. Angew. Chem., Int. Ed. Engl. 1986, 25, 450; Babirad, S. A.; Wang, Y.; Kishi, Y. J. Org. Chem. 1987, 52, 1370; Bimwala, R. M.; Vogel, P. J. Org. Chem. 1992, 57, 2076; Dietrich, H.; Schmidt, R. R. Liebigs Ann. Chem. 1994, 975; Mallet, A.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron Asymm. 1994, 5, 2593; Paton, R. M.; Penman, K. J. Tetrahedron Lett. 1994, 35, 3163; Mazéas, D.; Skrydstrup, T.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1995, 34, 909; Eyrisch, O.; Fessner, W.-D. Ibid. 1995, 34, 1639; Sarabia-Garcia, F.; López-Herrera, F. J.; Pino González, M. S. Tetrahedron 1995, 51, 5491 and references cited in these papers.
13. See e.g., Aebischer, B.; Bieri, J. H.; Prewo, R.; Vasella, A. Helv. Chim. Acta 1982, 65, 2251; Rouzaud, D.; Sinay, P. J. Chem. Soc., Chem. Commun. 1983, 1353; Giese, B.; Witzel, T. Angew. Chem., Int. Ed. Engl. 1986, 25, 450; Babirad, S. A.; Wang, Y.; Kishi, Y. J. Org. Chem. 1987, 52, 1370; Bimwala, R. M.; Vogel, P. J. Org. Chem. 1992, 57, 2076; Dietrich, H.; Schmidt, R. R. Liebigs Ann. Chem. 1994, 975; Mallet, A.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron Asymm. 1994, 5, 2593; Paton, R. M.; Penman, K. J. Tetrahedron Lett. 1994, 35, 3163; Mazéas, D.; Skrydstrup, T.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1995, 34, 909; Eyrisch, O.; Fessner, W.-D. Ibid. 1995, 34, 1639; Sarabia-Garcia, F.; López-Herrera, F. J.; Pino González, M. S. Tetrahedron 1995, 51, 5491 and references cited in these papers.
14. See e.g., Aebischer, B.; Bieri, J. H.; Prewo, R.; Vasella, A. Helv. Chim. Acta 1982, 65, 2251; Rouzaud, D.; Sinay, P. J. Chem. Soc., Chem. Commun. 1983, 1353; Giese, B.; Witzel, T. Angew. Chem., Int. Ed. Engl. 1986, 25, 450; Babirad, S. A.; Wang, Y.; Kishi, Y. J. Org. Chem. 1987, 52, 1370; Bimwala, R. M.; Vogel, P. J. Org. Chem. 1992, 57, 2076; Dietrich, H.; Schmidt, R. R. Liebigs Ann. Chem. 1994, 975; Mallet, A.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron Asymm. 1994, 5, 2593; Paton, R. M.; Penman, K. J. Tetrahedron Lett. 1994, 35, 3163; Mazéas, D.; Skrydstrup, T.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1995, 34, 909; Eyrisch, O.; Fessner, W.-D. Ibid. 1995, 34, 1639; Sarabia-Garcia, F.; López-Herrera, F. J.; Pino González, M. S. Tetrahedron 1995, 51, 5491 and references cited in these papers.
15. See e.g., Aebischer, B.; Bieri, J. H.; Prewo, R.; Vasella, A. Helv. Chim. Acta 1982, 65, 2251; Rouzaud, D.; Sinay, P. J. Chem. Soc., Chem. Commun. 1983, 1353; Giese, B.; Witzel, T. Angew. Chem., Int. Ed. Engl. 1986, 25, 450; Babirad, S. A.; Wang, Y.; Kishi, Y. J. Org. Chem. 1987, 52, 1370; Bimwala, R. M.; Vogel, P. J. Org. Chem. 1992, 57, 2076; Dietrich, H.; Schmidt, R. R. Liebigs Ann. Chem. 1994, 975; Mallet, A.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron Asymm. 1994, 5, 2593; Paton, R. M.; Penman, K. J. Tetrahedron Lett. 1994, 35, 3163; Mazéas, D.; Skrydstrup, T.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1995, 34, 909; Eyrisch, O.; Fessner, W.-D. Ibid. 1995, 34, 1639; Sarabia-Garcia, F.; López-Herrera, F. J.; Pino González, M. S. Tetrahedron 1995, 51, 5491 and references cited in these papers.
16. See e.g., Aebischer, B.; Bieri, J. H.; Prewo, R.; Vasella, A. Helv. Chim. Acta 1982, 65, 2251; Rouzaud, D.; Sinay, P. J. Chem. Soc., Chem. Commun. 1983, 1353; Giese, B.; Witzel, T. Angew. Chem., Int. Ed. Engl. 1986, 25, 450; Babirad, S. A.; Wang, Y.; Kishi, Y. J. Org. Chem. 1987, 52, 1370; Bimwala, R. M.; Vogel, P. J. Org. Chem. 1992, 57, 2076; Dietrich, H.; Schmidt, R. R. Liebigs Ann. Chem. 1994, 975; Mallet, A.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron Asymm. 1994, 5, 2593; Paton, R. M.; Penman, K. J. Tetrahedron Lett. 1994, 35, 3163; Mazéas, D.; Skrydstrup, T.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1995, 34, 909; Eyrisch, O.; Fessner, W.-D. Ibid. 1995, 34, 1639; Sarabia-Garcia, F.; López-Herrera, F. J.; Pino González, M. S. Tetrahedron 1995, 51, 5491 and references cited in these papers.
17. See e.g., Aebischer, B.; Bieri, J. H.; Prewo, R.; Vasella, A. Helv. Chim. Acta 1982, 65, 2251; Rouzaud, D.; Sinay, P. J. Chem. Soc., Chem. Commun. 1983, 1353; Giese, B.; Witzel, T. Angew. Chem., Int. Ed. Engl. 1986, 25, 450; Babirad, S. A.; Wang, Y.; Kishi, Y. J. Org. Chem. 1987, 52, 1370; Bimwala, R. M.; Vogel, P. J. Org. Chem. 1992, 57, 2076; Dietrich, H.; Schmidt, R. R. Liebigs Ann. Chem. 1994, 975; Mallet, A.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron Asymm. 1994, 5, 2593; Paton, R. M.; Penman, K. J. Tetrahedron Lett. 1994, 35, 3163; Mazéas, D.; Skrydstrup, T.; Beau, J.-M. Angew. Chem., Int. Ed. Engl. 1995, 34, 909; Eyrisch, O.; Fessner, W.-D. Ibid. 1995, 34, 1639; Sarabia-Garcia, F.; López-Herrera, F. J.; Pino González, M. S. Tetrahedron 1995, 51, 5491 and references cited in these papers.
18. Wei, A.; Haudrechy, A.; Audin, C.; Jun, H.-S.; Haudrechy-Bretel, N.; Kishi, Y. J. Org. Chem. 1995, 60, 2160 and ref. cited therein.
19. See e.g.: a) Kishi, Y. Pure & Appl. Chem. 1993, 65, 771; Wei, A.; Kishi, Y. J. Org. Chem. 1994, 59, 88; Martin, O. R.; Lai, W. Ibid. 1990, 55, 5188; 1993, 58, 176; O'Leary, D. J.; Kishi, Y. Tetrahedron Lett. 1994, 35, 5591; López-Herrera, F. J.; Pino-González, M. S.; Planas-Ruiz, F. Tetrahedron: Asymmetry 1990, 1, 465; b) Ferritto, R.; Vogel, P. Ibid. 1994, 5, 2077; c) Wei, A.; Boy, K. M.; Kishi, Y. J. Am. Chem. Soc. 1995, 117, 9432.
20. See e.g.: a) Kishi, Y. Pure & Appl. Chem. 1993, 65, 771; Wei, A.; Kishi, Y. J. Org. Chem. 1994, 59, 88; Martin, O. R.; Lai, W. Ibid. 1990, 55, 5188; 1993, 58, 176; O'Leary, D. J.; Kishi, Y. Tetrahedron Lett. 1994, 35, 5591; López-Herrera, F. J.; Pino-González, M. S.; Planas-Ruiz, F. Tetrahedron: Asymmetry 1990, 1, 465; b) Ferritto, R.; Vogel, P. Ibid. 1994, 5, 2077; c) Wei, A.; Boy, K. M.; Kishi, Y. J. Am. Chem. Soc. 1995, 117, 9432.
21. See e.g.: a) Kishi, Y. Pure & Appl. Chem. 1993, 65, 771; Wei, A.; Kishi, Y. J. Org. Chem. 1994, 59, 88; Martin, O. R.; Lai, W. Ibid. 1990, 55, 5188; 1993, 58, 176; O'Leary, D. J.; Kishi, Y. Tetrahedron Lett. 1994, 35, 5591; López-Herrera, F. J.; Pino-González, M. S.; Planas-Ruiz, F. Tetrahedron: Asymmetry 1990, 1, 465; b) Ferritto, R.; Vogel, P. Ibid. 1994, 5, 2077; c) Wei, A.; Boy, K. M.; Kishi, Y. J. Am. Chem. Soc. 1995, 117, 9432.
22. See e.g.: a) Kishi, Y. Pure & Appl. Chem. 1993, 65, 771; Wei, A.; Kishi, Y. J. Org. Chem. 1994, 59, 88; Martin, O. R.; Lai, W. Ibid. 1990, 55, 5188; 1993, 58, 176; O'Leary, D. J.; Kishi, Y. Tetrahedron Lett. 1994, 35, 5591; López-Herrera, F. J.; Pino-González, M. S.; Planas-Ruiz, F. Tetrahedron: Asymmetry 1990, 1, 465; b) Ferritto, R.; Vogel, P. Ibid. 1994, 5, 2077; c) Wei, A.; Boy, K. M.; Kishi, Y. J. Am. Chem. Soc. 1995, 117, 9432.
23. See e.g.: a) Kishi, Y. Pure & Appl. Chem. 1993, 65, 771; Wei, A.; Kishi, Y. J. Org. Chem. 1994, 59, 88; Martin, O. R.; Lai, W. Ibid. 1990, 55, 5188; 1993, 58, 176; O'Leary, D. J.; Kishi, Y. Tetrahedron Lett. 1994, 35, 5591; López-Herrera, F. J.; Pino-González, M. S.; Planas-Ruiz, F. Tetrahedron: Asymmetry 1990, 1, 465; b) Ferritto, R.; Vogel, P. Ibid. 1994, 5, 2077; c) Wei, A.; Boy, K. M.; Kishi, Y. J. Am. Chem. Soc. 1995, 117, 9432.
24. See e.g.: a) Kishi, Y. Pure & Appl. Chem. 1993, 65, 771; Wei, A.; Kishi, Y. J. Org. Chem. 1994, 59, 88; Martin, O. R.; Lai, W. Ibid. 1990, 55, 5188; 1993, 58, 176; O'Leary, D. J.; Kishi, Y. Tetrahedron Lett. 1994, 35, 5591; López-Herrera, F. J.; Pino-González, M. S.; Planas-Ruiz, F. Tetrahedron: Asymmetry 1990, 1, 465; b) Ferritto, R.; Vogel, P. Ibid. 1994, 5, 2077; c) Wei, A.; Boy, K. M.; Kishi, Y. J. Am. Chem. Soc. 1995, 117, 9432.
25. See e.g.: a) Kishi, Y. Pure & Appl. Chem. 1993, 65, 771; Wei, A.; Kishi, Y. J. Org. Chem. 1994, 59, 88; Martin, O. R.; Lai, W. Ibid. 1990, 55, 5188; 1993, 58, 176; O'Leary, D. J.; Kishi, Y. Tetrahedron Lett. 1994, 35, 5591; López-Herrera, F. J.; Pino-González, M. S.; Planas-Ruiz, F. Tetrahedron: Asymmetry 1990, 1, 465; b) Ferritto, R.; Vogel, P. Ibid. 1994, 5, 2077; c) Wei, A.; Boy, K. M.; Kishi, Y. J. Am. Chem. Soc. 1995, 117, 9432.
26. See e.g.: a) Kishi, Y. Pure & Appl. Chem. 1993, 65, 771; Wei, A.; Kishi, Y. J. Org. Chem. 1994, 59, 88; Martin, O. R.; Lai, W. Ibid. 1990, 55, 5188; 1993, 58, 176; O'Leary, D. J.; Kishi, Y. Tetrahedron Lett. 1994, 35, 5591; López-Herrera, F. J.; Pino-González, M. S.; Planas-Ruiz, F. Tetrahedron: Asymmetry 1990, 1, 465; b) Ferritto, R.; Vogel, P. Ibid. 1994, 5, 2077; c) Wei, A.; Boy, K. M.; Kishi, Y. J. Am. Chem. Soc. 1995, 117, 9432.
27. See e.g.: Higton, A. A.; Roberts, A. D. "Dictionary of Antibiotics and Related Substances", Bycroft, B. W. Ed.; Chapman & Hall, London, 1988; Suami, T. in "Carbohydrates, Synthetic Methods and Applications in Medicinal Chemistry", Ogura, H.; Hasegawa, A.; Suami, T. Eds.; Kodansha Ltd. & VCH, Tokyo, 1992; Bach, G.; Breiding-Mack, S.; Grabley, S.; Hammann, P.; Hütter, K.; Thiericke, R.; Uhr, H.; Wink, J.; Zeeck, A. Liebigs Ann. Chem. 1993, 241.
28. See e.g.: Higton, A. A.; Roberts, A. D. "Dictionary of Antibiotics and Related Substances", Bycroft, B. W. Ed.; Chapman & Hall, London, 1988; Suami, T. in "Carbohydrates, Synthetic Methods and Applications in Medicinal Chemistry", Ogura, H.; Hasegawa, A.; Suami, T. Eds.; Kodansha Ltd. & VCH, Tokyo, 1992; Bach, G.; Breiding-Mack, S.; Grabley, S.; Hammann, P.; Hütter, K.; Thiericke, R.; Uhr, H.; Wink, J.; Zeeck, A. Liebigs Ann. Chem. 1993, 241.
29. See e.g.: Higton, A. A.; Roberts, A. D. "Dictionary of Antibiotics and Related Substances", Bycroft, B. W. Ed.; Chapman & Hall, London, 1988; Suami, T. in "Carbohydrates, Synthetic Methods and Applications in Medicinal Chemistry", Ogura, H.; Hasegawa, A.; Suami, T. Eds.; Kodansha Ltd. & VCH, Tokyo, 1992; Bach, G.; Breiding-Mack, S.; Grabley, S.; Hammann, P.; Hütter, K.; Thiericke, R.; Uhr, H.; Wink, J.; Zeeck, A. Liebigs Ann. Chem. 1993, 241.
30. McCasland, G. E.; Furuta, S.; Durham, L. J. Org. Chem. 1966, 31, 1516.
31. Suami, T.; Ogawa, S. Adv. Carbohydr. Chem. Biochem. 1990, 48, 21.
32. Ferritto, R.; Vogel, P. Tetrahedron Lett. 1995, 36, 3517.
33. Cossy, J.; Ranaivosata, J.-L.; Bellosta, V.; Ancerewicz, J.; Ferritto, R.; Vogel, P. J. Org. Chem. in print.
34. Barbaud, C.; Bols, M.; Lundt, I.; Sierks, M. R. Tetrahedron 1995, 51, 9063.
35. 2C(3)).
36. 3).
37. 3).
38. +•).
39. H: 6.09 (d, 2.4, HC(2)), 5.40 (t, 3.0), 5.23 (dd, 8.7, 4.1), 5.21 (dd, 8.7, 3.0), 5.1 (t, 2.7, HC(5)), 4.47 (dd, 11.6, 7.9), 4.37 (m), 4.20 (m), 4.05 (dd, 9.1, 2.4, HC(3)), 4.02 (d, 2.7, HC(6)), 3.99 (dd, 11.6, 4.8), 2.13, 2.085, 2.083, 2.07, 2.05 (5s, 5 OAc), 2.13-2.05 (m, HC(4), H-CH-C(4)), 1.38-1.32 (m, H-CH-C(4)).
40. 2C(4)).
41. All new compounds presented here gave satisfactory elemental analyses.