Efficient synthesis of polyfunctionalised enantiopure diazepanone scaffolds

Tetrahedron Letters

Volumn 48, Issue 46, 2007, Pages 8149-8152

  Monasson, Olivier ^a   Ginisty, Maryon ^a   Bertho, Gildas ^a   Gravier Pelletier, Christine ^a   Le Merrer, Yves ^a  

^a UNIVERSITÉ PARIS DESCARTES   (France)

Author keywords

Epoxide opening; Lactamisation; Lactonisation; Scaffolds; Translocase MraY

Indexed keywords

1,4 DIAZEPAN 3 ONE; AMINE; ANTIINFECTIVE AGENT; ASCORBIC ACID; EPOXIDE; ISOASCORBIC ACID; SERINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHIRALITY; DRUG SYNTHESIS; LACTONIZATION;

EID: 35348865461     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.09.098     Document Type: Article

References (21)

1. Glenn M.P., and Fairlie D.P. Mini Rev. Med. Chem. 2 (2002) 433-445 and the following articles of this review dedicated to peptidomimetics
2. Meutermans W., Thanh L.G., and Becker B. ChemMedChem 1 (2006) 1164-1194
3. van Heijnoort J. Nat. Prod. Rep. 8 (2001) 503-519
4. Boyle D.S., and Donachie W.D. J. Bacteriol. 180 (1998) 6429-6432
5. Bouhss A., Mengin-Lecreulx D., Le Beller D., and van Heijenoort J. Mol. Microbiol. 34 (1999) 576-585
6. Bouhss A., Crouvoisier M., Blanot D., and Mengin-Lecreulx D. J. Biol. Chem. 279 (2004) 29974-29980
7. Stachyra T., Dini C., Ferrari P., Bouhss A., van Heijenoort J., Mengin-Lecreulx D., Blanot D., Biton J., and Le Beller D. Antimicrob. Agents Chemother. 48 (2004) 897-902
8. Isono K., Uramoto M., Kusakabe H., Kimura K., Izaki K., Nelson C.C., and McCloskey J.A. J. Antibiot. 38 (1985) 1617-1621
9. For scaffolds with a seven-membered diazepane ring, see for example:. Giovannoni J., Subra G., Amblard M., and Martinez J. Tetrahedron Lett. 42 (2001) 5389-5392
10. Hirokawa Y., Horikawa T., Noguchi H., Yamamoto K., and Kato S. Org. Proc. Res. Dev. 6 (2002) 28-35
11. Lampariello L.R., Piras D., Rodriquez M., and Taddei M. J. Org. Chem. 68 (2003) 7893-7895
12. Iden H.S., and Lubell W.D. Org. Lett. 8 (2006) 3425-3428
13. Liang G.-B., Qian X., Feng D., Biftu T., Eiermann G., He H., Leiting B., Lyons K., Petrov A., Sinha-Roy R., Zhang B., Wu J., Zhang X., Thornberry N.A., and Weber A.E. Bioorg. Med. Chem. Lett. 17 (2007) 1903-1907
14. For a review on MraY inhibitors, see:. Dini C. Curr. Top. Med. Chem. 5 (2005) 1221-1236 and references cited therein
15. Gravier-Pelletier C., Charvet I., Le Merrer Y., and Depezay J.C. J. Carbohydr. Chem. 16 (1997) 129-141
16. Freidinger R.M., Hinkle J.S., Perlow D.S., and Arison B.H. J. Org. Chem. 48 (1983) 77-81
17. Abushanab E., Vemishetti P., Leiby R.W., Singh H.K., Mikkilineni A.B., Wu D.C.J., Saibaba R., and Panzica R.P. J. Org. Chem. 53 (1988) 2598-2602
18. Le Merrer Y., Gravier-Pelletier C., Guerrouache M., and Depezay J.C. Tetrahedron Lett. 39 (1998) 385-388
19. Kolb C.H., and Sharpless K.B. Tetrahedron 48 (1992) 10515
20. ®). However, yield was not improved and part of starting material was always recovered.
21. Dauber-Osguthorpe P., Roberts V.A., Osguthorpe D.J., Wolff J., Genest M., and Hagler A.T. Proteins: Struct. Funct. Genet. 4 (1988) 31-47