Synthesis of rhamnosylated diosgenyl glucosides as mimetics of cytostatic steroidal saponins from Ornithogalum saundersiae and Galtonia candicans

Organic and Biomolecular Chemistry

Volumn 1, Issue 24, 2003, Pages 4373-4379

  Suhr, René ^a   Pfefferkorn, Pascal ^a   Weingarten, Saskia ^a   Thiem, Joachim ^a  

^a UNIVERSITY OF HAMBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLATION; BIOCHEMISTRY; BIOSYNTHESIS; CHEMICAL ACTIVATION; ESTERS; GLUCOSE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

COUPLING CONSTANT; GLUCOSYLATION;

DRUG PRODUCTS;

GALTONIA CANDICANS; HOMO; ORNITHOGALUM;

DIOSGENIN; GLUCOSIDE; SAPONIN;

ANGIOSPERM; ARTICLE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; GLYCOSYLATION; STEREOISOMERISM; SYNTHESIS;

CARBOHYDRATE CONFORMATION; DIOSGENIN; GLUCOSIDES; GLYCOSYLATION; LILIACEAE; MODELS, CHEMICAL; MOLECULAR STRUCTURE; SAPONINS; STEREOISOMERISM;

EID: 0346276890     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b309066c     Document Type: Article

References (19)

1. Y. Mimaki, M. Kuroda, Y. Sashida, T. Hirano, K. Oka, A. Dobashi, H. Koshino and J. Uzawa, Tetrahedron Lett., 1996, 37, 1245-1248.
2. Y. Mimaki, M. Kuroda, Y. Sashida, T. Yarnori and T. Tsuruo, Helv. Chim. Acta, 2000, 83, 2698-2704.
3. R. Suhr, Doctoral Thesis, University of Hamburg, Hamburg, 2001; Abstract: http://www.sub.uni-hamburg.de/disse/848/zusammen.pdf; Full Text: http://www.sub.uni-hamburg.de/disse/848/dissertation.pdf.
4. M. Lahmann, H. Gybäck, P. J. Garegg, S. Oscarson, R. Suhr and J. Thiem, Carbohydr. Res., 2002, 337, 2153-2159.
5. R. Suhr, M. Lahmann, S. Oscarson and J. Thiem, Eur. J. Org. Chem., 2003, 4003-4011.
6. A. S. Perlin and B. Casu, Tetrahedron Lett., 1969, 2921-2924.
7. K. Bock and C. Pedersen, J. Chem. Soc., Perkin Trans. 2, 1974, 293-297.
8. V. Pozsgay and H. J. Jennings, J. Org. Chem., 1988, 53, 4042-4052.
9. H. M. Zuurmond, G. H. Veeneman, G. A. van der Marel and J. H. van Boom, Carbohydr. Res., 1993, 241, 153-164.
10. E. Fischer, M. Bergmann and H. Rabe, Ber. Dtsch. Chem. Ges., 1920, 53, 2362-2388.
11. V. Pozsgay and A. Neszmélyi, Carbohydr. Res., 1980, 80, 196-202.
12. N. K. Kochetkov, L. V. Backinowsky and Y. E. Tsvetkov, Tetrahedron Lett., 1977, 41, 3681-3684.
13. G. H. Veeneman, S. H. van Leeuwen and J. H. van Boom, Tetrahedron Lett., 1990, 31, 1331-1334.
14. H. M. Zuurmond, G. A. van der Marel and J. H. van Boom, Red. Trav. Chim. Pays-Bas, 1993, 112, 507-510.
15. H. E. Gottlieb, V. Kotlyar and A. Nudelman, J. Org. Chem., 1997, 62, 7512-7515.
16. S. A. McLuckey and J. M. Wells, Chem. Rev., 2000, 100, 1-36.
17. M. Ravenscroft, R. M. G. Roberts and J. G. Tillett, J. Chem. Soc., Perkin Trans. 2, 1982, 1569-1572.
18. S. Komiya, Synthesis of Organometallic Compounds - A Practical Guide, John Wiley & Sons, Chichester, 1997, pp. 35-56.
19. J. Conchie, G. A. Levvy and C. A. Marsh, Adv. Carbohydr. Chem., 1957, 12, 157-187.