Enantioselective synthesis of iclaprim enantiomers- A versatile approach to 2-substituted chiral chromenes

Journal of Organic Chemistry

Volumn 75, Issue 11, 2010, Pages 3781-3785

  Tahtaoui, Chouaib ^a   Demailly, Arnold ^a   Guidemann, Carole ^a   Joyeux, Cécile ^b   Schneider, Peter ^a  

^a Arpida Ltd   (Switzerland)

^b Ecole Nationale Superieure de Chimie de Mulhouse   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CHROMENES; CYCLOPROPYL; DIAMINOPYRIMIDINE; ENANTIOSELECTIVE SYNTHESIS; HETEROCYCLES; HOMOALLYL ALCOHOL; INVERSION OF CONFIGURATION; MITSUNOBU REACTIONS;

CHIRALITY; ENANTIOMERS; ENANTIOSELECTIVITY; SYNTHESIS (CHEMICAL);

CYCLIZATION;

ALCOHOL DERIVATIVE; CHROMENE DERIVATIVE; CYCLOPROPYL HOMOALLYL ALCOHOL DERIVATIVE; ICLAPRIM; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; ENANTIOMER; ENANTIOSELECTIVITY; MITSUNOBU REACTION; NONHUMAN;

ALCOHOLS; BENZOPYRANS; FOLIC ACID ANTAGONISTS; PYRIMIDINES; STEREOISOMERISM; TETRAHYDROFOLATE DEHYDROGENASE;

EID: 77952969414     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100566c     Document Type: Article

References (27)

1. Kompis, I. M.; Islam, K.; Then, R. L. Chem. Rev. 2005, 105, 593-620
2. Masciadri, R. U.S. Patent 5,773,446; Hoffmann-La Roche, June 30, 1998.
3. Schneider, P.; Hawser, S.; Islam, K. Bioorg. Med. Chem. Lett. 2003, 13, 4217-4221
4. Hartmann, P. G.; Kompis, I. M.; Jaeger, J.; Mukhija, S.; Islam, K. Abstracts, F2020, 42nd Interscience Conference on Antimicrobial Agents and Chemotherapy, San Diego, CA, Sept 27-30, 2002; American Society for Microbiology: Washington, DC, 2002.
5. Kazuo, M.; Kazuya, O.; Hironobu, H. J. Org. Chem. 1989, 54, 557-560
6. Ishikawa, T. Heterocycles 2000, 53, 453-473
7. Wipf, P.; Weiner, W. S. J. Org. Chem. 1999, 64, 5321-5324
8. Oliveira, M. M.; Moustrou, C.; Carvalho, L. M.; Silva, J. A. C.; Samat, A.; Guglielmetti, R.; Dubest, R.; Aubard, J.; Oliveira-Campos, A. M. F. Tetrahedron 2002, 58, 1709-1718
9. Hardouin, C.; Burgaud, L.; Valleix, A.; Doris, E. Tetrahedron Lett. 2003, 44, 435-437
10. Goujon, J.-Y.; Zammatio, F.; Chrétien, J.-M.; Beaudet, I. Tetrahedron 2004, 60, 4037-4049
11. Chang, S.; Grubbs, R. H. J. Org. Chem. 1998, 63, 864-866
12. Hodgetts, K. J. Tetrahedron 2005, 61, 6860-6870
13. Kawasaki, M.; Kakuda, H.; Goto, M.; Kawabata, S.; Kometani, T. Tetrahedron: Asymmetry 2003, 14, 1529-1534
14. Varadarajan, S.; Mohapatra, D. K.; Datta, A. Tetrahedron Lett. 1998, 39, 1075-1078
15. Schoffers, E.; Golebiowski, A.; Johnson, C. R. Tetrahedron 1996, 52, 3769-3826
16. Burgess, K.; Jennings, L. D. J. Am. Chem. Soc. 1991, 113, 6129-6139
17. Wang, Y.-F.; Lalonde, J. J.; Momongan, M.; Bergbreiter, D. A.; Wong, C.-H. J. Am. Chem. Soc. 1988, 110, 7200-7205
18. Brown, H. C.; Randad, R. S.; Bhat, K. S.; Zaidlewicz, M.; Racherla, U. S. J. Am. Chem. Soc. 1990, 112, 2389-2392
19. Ramachandran, P. V. Aldrichim. Acta 2002, 35, 23-35
20. Kim, M. J.; Kim, J. Y. J. Chem. Soc., Chem. Commun. 1991, 5, 326-7
21. Kutner, A.; Martynow, J.; Chodynski, M.; Szelejewski, W.; Fitak, H.; Krup, M. WO 03/087048 A2, Instytut Farmaceutyczny, October 23, 2003.
22. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092-4096
23. Olah, G. A.; Prakash Reddy, V.; Surya Prakash, G. K. Chem. Rev. 1992, 92, 69-95
24. Olah, G. A.; Surya Prakash, G. K.; Rasul, G. J. Am. Chem. Soc. 2008, 130, 9168-9172
25. Choi, E. T.; Kang, K. H.; Lee, M. H.; Park, Y. S. Bull. Korean Chem. Soc. 2008, 29, 859-862
26. Shintou, T.; Mukaiyama, T. J. Am. Chem. Soc. 2004, 126, 7359-67
27. Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 1998, 120, 9074-9075