A polyhydroxylated cyclopentene: A useful synthon toward the synthesis of carbocyclic D-fructofuranoid

Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences

Volumn 54, Issue 4, 1999, Pages 565-568

  Seepersaud, Mohindra ^a   Bucala, Richard ^a   Al Abed, Yousef ^a  

^a PICOWER INST FOR MEDICAL RESEARCH   (United States)

Author keywords

D Arabino and D Fructofuranoid; Grubb's and Schrock's Catalyst; Polyhydroxylated Cyclopentene

Indexed keywords

CHEMISTRY;

CYCLOPENTENES; POLYHYDROXYLATED; SYNTHONS;

HYDROXYLATION;

EID: 0039521558     PISSN: 09320776     EISSN: None     Source Type: Journal    
DOI: 10.1515/znb-1999-0422     Document Type: Article

References (22)

1. a) C. A. Hasemann, E. S. Istvan, K. Uyeda, J. Deisenhofer, Structure 4, 1017 (1996);
2. b) S. J. Pilkis, T. H. Claus, I. J. Kurland, A. J. Lange, Ann. Rev. Biochem. 64, 799 (1995);
3. c) G. G. Rousseau, L. Hue, Prog. Nucl. Acid Res. Mol. Biol. 45, 99 (1993);
4. d) K. Uyeda, In Study of Enzymes II. (Kuby S. A., ed.) 445 (1991).
5. a) D. M. Nathan, Ann. Int. Med. 124, 86 (1996);
6. b) M. Nishimura, S. Federov, K. Uyeda J. Biol. Chem. 269, 26100 (1994).
7. a) J. Chesney, R. Mitchell, F. Benigni, M. Bacher, L. Spiegel, Y. Al-Abed, J. Hee Han, C. Metz, R. Bucala, R. Proc. Natl. Acad. Sci. USA 6, 3047 (1999);
8. b) J. M. Argiles, B. Azcon-Biet, J. Mol and Cell. Biochem. 81, 3 (1988);
9. c) L. Hue, G. G. Rousseau, Adv. Enzyme Regul. 33, 97 (1993).
10. C. S. Wilcox, J. J. Guadino, J. Am. Chem. Soc. 108, 3102 (1986).
11. a) R. H. Grubbs, S. J. Miller, Acc. Chem. Res. 28, 446 (1995);
12. b) A. Furstner, K. Langemann, Synthesis 1997, 792;
13. c) K. C. Nicaloau, Y. He, D. Vouloumis, H. Vallberg, F. Roschangar, F. Sarabia, S. Ninkovic, Z. Yang, J. I. Trujillo, J. Am. Chem. Soc. 119, 10073 (1997);
14. d) M. T. Crimmins, A. L. Choy, J. Org. Chem. 62, 7548 (1997);
15. e) H. G. Schmalz, Angew. Chem., Int. Ed. Engl. 34, 1833 (1995);
16. f) M. Arisawa, E. Takezawa, A. Nishida, M. Miwako, M. Nakagawa, Synlett. 1179 (1997).
17. O. Sellier, P. Van de Weighe, L. D. Nouen, C. Strehler, J. Eustache, Tetrahedron Lett. 40, 853 (1999).
18. H. Ovaa, M. A. Leeeuwenburgh, H. S. Overkleeft, G. A. van der Marel, J. H. van Boom, Tetrahedron Lett. 39, 3025 (1998).
19. F. Freeman, R. D. Robarge, Carbohydr. Res. 154, 270 (1986).
20. This compound is available from Strem Chemicals.
21. M. Seepersaud, D. R. Mootoo, M. Blumenstein, Tetrahedron 53, 5711 (1997).
22. R. J. Nachman, M. Honel, T. M. Williams, R. C. Halaska, H. S. Mosher, J. Org. Chem. 51, 4802 (1986). This compound is available from Pfanstiehl Laboraties, Inc., cat. no. D-115.