Synthetic route towards (5R,2′S,5′S,6′S)-ribosyl-diazepanone, an analogue core of the liposidomycins

Tetrahedron Asymmetry

Volumn 18, Issue 16, 2007, Pages 1955-1963

  Drouillat, Bruno ^a   Bourdreux, Yann ^a   Perdon, Delphine ^a   Greck, Christine ^a  

^a UNIVERSITÉ DE VERSAILLES SAINT QUENTIN EN YVELINES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

4 TRIISOPROPYLSILYLOXY 3 OXOBUTANOATE; ALDEHYDE DERIVATIVE; ANTIBIOTIC AGENT; BUTYRIC ACID DERIVATIVE; ESTER DERIVATIVE; FURAN DERIVATIVE; LIPOSIDOMYCIN; METHYL 5 O (2 METHOXYETHOXYMETHYL) 5 C[(2 METHOXYETHOXYMETHOXY) 5' (2 METHOXYETHOXYMETHOXYMETHYL) 1' METHYL 3' OXO 1',4' DIAZEPAN 2' YL] 2,3 O ISOPROPYLIDENE BETA DEXTRO RIBOFURANOSIDE; NUCLEOSIDE DERIVATIVE; RIBOSE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL;

EID: 34548543864     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2007.07.023     Document Type: Article

References (33)

1. Isono K., Uramoto M., Kusakabe H., Kimura K., Izaki K., Nelson C.C., and McCloskey J.A. J. Antibiot. 38 (1985) 1617-1621
2. Silver L.L. Curr. Opin. Microbiol. 6 (2003) 431-438
3. Kimura K., and Bugg T.D.H. Nat. Prod. Rep. 20 (2003) 252-273
4. Brandish P.E., Kimura K., Inukai M., Southgate R., Lonsdale J.T., and Bugg T.D.H. Antimicrob. Agents Chemother. 40 (1996) 1640-1644
5. Ubukata M., Isono K., Kimura K., Nelson C.C., and McCloskey J.A. J. Am. Chem. Soc. 110 (1988) 4416-4417
6. Ubukata M., Kimura K., Isono K., Gregson J.M., and McCloskey J.A. J. Org. Chem. 57 (1992) 6392-6403
7. Spada M.R., Ubukata M., and Isono K. Heterocycles 34 (1992) 1147-1167
8. Kim K.S., and Ahn Y.H. Tetrahedron: Asymmetry 9 (1998) 3601-3605
9. Le Merrer Y., Gravier-Pelletier C., Gerrouache M., and Depezay J.-C. Tetrahedron Lett. 39 (1998) 385-388
10. Gravier-Pelletier C., Milla M., Le Merrer Y., and Depezay J.-C. Eur. J. Org. Chem. 16 (2001) 3089-3096
11. Sarabia F., Martin-Ortiz L., and Lopez-Herrera F. Org. Lett. 5 (2003) 3927-3930
12. Knapp S., Moriello G.J., and Doss G.A. Org. Lett. 4 (2002) 603-606
13. Miyake, T.; Igarashi, M.; Shidara, T.; Takahashi, Y. JP WO 2004-067544A1, 2004.
14. Hirano S., Ichikawa S., and Matsuda A. Angew. Chem., Int. Ed. 44 (2005) 1854-1856
15. Greck C., Bischoff L., Ferreira F., Pinel C., Piveteau E., and Genêt J.P. Synlett (1993) 475-477
16. Greck C., Drouillat B., and Thomassigny C. Eur. J. Org. Chem. 7 (2004) 1377-1385 and references cited therein
17. Genêt J.P., Pinel C., Ratovelomanana-Vidal V., Mallart S., Pfister X., Cano De Andrade M.C., and Laffitte J.A. Tetrahedron: Asymmetry 5 (1994) 665-674
18. Genêt J.P., Ratovelomanana-Vidal V., Caňo de Andarade C., Pfister X., Guerreiro P., and Lenoir J.Y. Tetrahedron Lett. 36 (1995) 4801-4804
19. Ratovelomanana-Vidal V., and Genêt J.P. J. Organomet. Chem. 567 (1998) 163-171
20. Drouillat B., Poupardin O., Bourdreux Y., and Greck C. Tetrahedron Lett. 44 (2003) 2781-2783
21. O'Donnel M.J., and Polt R.L. J. Org. Chem. 47 (1982) 2663-2666
22. Chruma J.J., Sames D., and Polt R. Tetrahedron Lett. 38 (1997) 5085-5086
23. Bourdreux Y., Drouillat B., and Greck C. Synlett (2005) 2086-2088
24. 2 catalyst.
25. Guanti G., Banfi L., and Narisano E. Tetrahedron Lett. 30 (1989) 5507-5510
26. Crouch R.D. Tetrahedron: Asymmetry 28 (2004) 5833-5871
27. In: Greene T.W., and Wuts P.G.M. (Eds). Protective Groups in Organic Synthesis. 3rd ed. (1999), John Wiley & Sons, New York
28. Nelson T.D., and Crouch R.D. Synthesis 9 (1996) 1031-1069
29. Bourdreux Y., Drouillat B., and Greck C. Lett. Org. Chem. 3 (2006) 368-370
30. Abdel-Magid A.F., Caron K.G., Harris B.D., Maryanoff C.A., and Shah R.D. J. Org. Chem. 61 (1996) 3849-3862
31. In: Aramarego W.L.F., and Perrin D.D. (Eds). Purification of Laboratory Chemicals. 4th ed. (1996), Butterworth Heinemann
32. Brooks D.W., Lu L.D.L., and Masamune S. Angew. Chem., Int. Ed. Engl. 1 (1979) 72-74
33. Hampton A., Perini F., and Harper P.J. Carbohydr. Res. 37 (1974) 359-367