A stereoselective route to bioactive nucleotide phosphonate analogs

Tetrahedron Letters

Volumn 44, Issue 45, 2003, Pages 8261-8263

  Bubenik, Monica ^a   Préville, Patrice ^a   Dugas, Josée ^a   Attardo, Giorgio ^a   Chan, Laval ^a  

^a Shire Canada   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIVIRUS AGENT; PHOSPHONIC ACID DERIVATIVE; TETRAHYDROFURAN DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CIS TRANS ISOMERISM; DRUG SYNTHESIS; ENANTIOSELECTIVITY; GAS CHROMATOGRAPHY; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0141992092     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.09.071     Document Type: Article

References (18)

1. Valerianova M., Vortuba I., Holy A., Mandys V., Otova B. Anticancer Res. 21:2001;2057.
2. Pisarev V.M., Lee S., Connelly M.C., Fridland A. Mol. Pharmacol. 52:1997;63.
3. Elliot R.D., Rener G.A., Riordan J.M., Secrist J.A., Bennett L.L., Parker W.B., Montgomery J.A. J. Med. Chem. 37:1994;739.
4. Nguyen-Ba P., Turcotte N., Yuen L., Bédard J., Quimpère M., Chan L. Bioorg. Med. Chem. Lett. 8:1998;3561.
5. Bédard J., May S., Lis M., Tryphonas L., Drach J., Huffman J., Sidwell R., Chan L., Bowlin T., Rando R. Antimicrob. Agents. Chemother. 43:1999;557.
6. Leblond L., Attardo G., Hamelin B., Bouffard D.Y., Nguyen-Ba N., Goudreau H. Mol. Cancer Ther. 1:(9):2002;737.
7. Bubenik M., Rej R., Nguyen-Ba N., Attardo G., Oeullet F., Chan L. Bioorg Med. Chem. Lett. 12:2002;3063.
8. Rychnovsky S.D., Bartlett P.A. J. Am. Chem. Soc. 103:1981;3963.
9. Marek I., Lefrancois J.-M, Normant J-F. Tetrahedron Lett. 33:1992;1747.
10. Arbuzov B.A., Zoroatrova V.M., Tudrin G.A., Fuzhenkova A.V. Izv. Akad. Nauk S.S.S.R. (Trans.). 23:1974;2541.
11. The catalyst was prepared according to procedures descibed in: Mathre D.J., Jones T.K., Xavier L.C., Blacklock T.J., Reamer R.A., Mohan J.J., Jones E.T.T., Hoogsteen K., Baum M.W., Grabowski E.J.J. J. Org. Chem. 56:1991;751.
12. Meier C., Laux W.H.G. Tetrahedron. 52:1996;589.
13. 31P NMR (400 MHz, CDCl3): 24.5 ppm.
14. Corey E.J., Helal C.J. Angew. Chem., Int. Ed. Engl. 37:1998;1986.
15. Cyclization with iodine resulted in poor selectivities and yields.
16. 3): 21.6 ppm.
17. Armstrong A., Brackenridge I., Jackson R.F.W., Kirk J.M. Tetrahedron Lett. 29:1988;2483-2486.
18. 31P NMR intensities.