New syntheses of two epimers of (+)-castanospermine: (+)-8a-Epi- and (+)-1,8a-Di-epi-castanospermine

Tetrahedron

Volumn 55, Issue 7, 1999, Pages 2061-2076

  Bartnicka, Ewa ^a   Zamojski, Aleksander ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

CASTANOSPERMINE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; COMPETITIVE INHIBITION; DRUG ISOLATION; DRUG SYNTHESIS; LEGUME; PLANT SEED; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0033548012     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)01218-6     Document Type: Article

References (23)

1. Hohenschutz, L. D.; Bell, E. A.; Jewess, P. J.; Leworthy, D. P.; Pryce, R. J.; Arnold, E.; Clardy, J. Phytochemistry 1981, 20, 811-814.
2. Nash, R. J.; Fellows, L. E.; Dring, J. V.; Stirton, C. H.; Carter, D.; Hegarty, M. P.; Bell, E. A. Phytochemistry 1988, 27, 1403-1404.
3. Trugman, G.; Rousset, M.; Zweibaum, A. FEBS Lett., 1986, 195, 28-32.
4. Sasak, V. W.; Ordovas, J. M.; Elbein, A. D.; Berningen, R. W. Biochem. J. 1985, 232, 759-766.
5. Ostrander, G. K.; Scribner, N. K.; Rohrschneider, L. R. Cancer Res. 1988, 48, 1091-1094.
6. Truscheit, E.; Frommer, W.; Junge, B.; Muller, L.; Schmidt, D. D.; Wingender, W. Angew. Chem. Int. Ed. Engl. 1981, 20, 744-762.
7. Nichols, E. J.; Manger, R.; Hakomori, S.; Herscovics, A.; Rohrschneider, L. R. Molec. Cell. Biol. 1985, 5, 3467-3471.
8. Walker, B. D.; Kowalski, M.; Goh, W. C.; Kozarsky, K.; Krieger, M.; Rosen, C.; Rohrschneider, L. R.; Haseltine, W. A.; Sodroski, J. Proc. Natl.. Acad Sci. U.S.A. 1987, 84, 8120-8124.
9. Ruprecht, R. M.; Mullaney, S.; Andersen, J.; Bronson, R. J. Acquired Immune Defic. Syndr. 1989, 2, 149-157.
10. Molyneux, R. J.; Roitman, J. N.; Dunnheim, G.; Szumilo, T.; Elbein, A. D. Arch. Biochem. Biophys. 1986, 251, 450-457.
11. Molyneux, R. J.; Pan, Y. T.; Tropea, J. E.; Benson, M.; Kaushal, G. P.; Elbein, A. D. Biochemistry 1991, 30, 9981-9987.
12. Fleet, G. W. J.; Ramsden, N. G.; Molyneux, R. J.; Jacob, G. S. Tetrahedron Lett. 1988, 29, 3603-3606.
13. Fleet, G. W. J.; Ramsden, N. G.; Nash, R. J.; Fellows, L. E.; Jacob, G. S.; Molyneux, R. J.; Cenci di Bello, I.; Winchester, B. Carbohydrate Res. 1990, 205, 269-282.
14. Burgess, K.; Henderson, I. Tetrahedron, 1992, 48, 4045-4066.
15. Cossy, J.; Vogel, P. Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1993; pp. 275-363.
16. Izquierdo, I.; Plaza, M. T.; Robles, R.; Mota, A. J. Tetrahedron: Asymmetry, 1998, 9, 1015-1027. Cf. also Furneaux, R. H.; Gainsford, G. J.; Mason, J. M.; Tyler, P. C.; Hartley, O.; Winchester, B. G. Tetrahedron, 1997, 53, 245-268 and the literature therein.
17. Izquierdo, I.; Plaza, M. T.; Robles, R.; Mota, A. J. Tetrahedron: Asymmetry, 1998, 9, 1015-1027. Cf. also Furneaux, R. H.; Gainsford, G. J.; Mason, J. M.; Tyler, P. C.; Hartley, O.; Winchester, B. G. Tetrahedron, 1997, 53, 245-268 and the literature therein.
18. Paquette, L. A., Ed., Encyclopedia of Reagents for Organic Synthesis, Wiley, Chichester 1995, Vol. 6, pp. 3694-3699.
19. Burgess, K.; Henderson, I.; Chaplin, D. C.; Pan, Y. T.; Elbein, A. D. J. Org. Chem. 1992, 57, 1103-1109.
20. Leeper, F. J.; Howard, S. Tetrahedron Lett. 1995, 36, 2335-2338.
21. Miller, S. A.; Chamberlin, A. R. J. Am. Chem. Soc. 1990, 112, 8100-8112.
22. Hashimoto, H.; Asano, K.; Fujii, F.; Yoshimura, J. Carbohydr. Res. 1982, 104, 87-104.
23. Pakulski, Z.; Zamojski, A. Tetrahedron 1995, 51, 871-908.