Stereoselective synthesis of a key intermediate of sanfetrinem by means of a chelated tin(IV) enolate

Journal of Organic Chemistry

Volumn 62, Issue 6, 1997, Pages 1653-1661

  Rossi, Tino ^a   Marchioro, Carla ^a   Paio, Alfrede ^a   Thomas, Russell J ^a   Zarantonello, Paola ^a  

^a GSK   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2 AZETIDINONE DERIVATIVE; SANFETRINEM;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030932639     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962095m     Document Type: Article

References (22)

1. (a) Tamburini, B.; Perboni, A.; Rossi, T.; Donati, D.; Andreotti, D.; Gaviraghi, G.; Carlesso, R; Bismara C. Eur. Pat. Appl. EP0416953 A2, 1991; Chem. Abstr. 1992, 116, 235337t.
2. (a) Tamburini, B.; Perboni, A.; Rossi, T.; Donati, D.; Andreotti, D.; Gaviraghi, G.; Carlesso, R; Bismara C. Eur. Pat. Appl. EP0416953 A2, 1991; Chem. Abstr. 1992, 116, 235337t.
3. (b) Perboni, A.; Rossi, T.; Gaviraghi, G.; Ursini, A.; Tarzia G. WO 9203437,
4. (c) Perboni, A.; Tamburini, B.; Rossi, T.; Donati, D.; Tarzia G.; Gaviraghi, G. In Recent Advances in the Chemistry of Anti-Infective Agents; Bentley, P. H., Ponsford, R., Eds.; RSC: Cambridge 1992; pp 21-35.
5. (d) Andreotti, D.; Rossi, T.; Gaviraghi, G.; Donati, D., Marchioro, C.; Di Modugno, E.; Perboni, A. D. Bioorg. Med. Chem. Lett. 1996, 6, 491.
6. Di Modugno, E.; Erbetti, I.; Ferrari, L.; Galassi, G. L.; Hammond, S. M.; Xerri, L. Antimicrob. Agents Chemother. 1994, 38, 2362.
7. Bismara, C.; Di Fabio, R.; Donati, D.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1995, 36, 4283.
8. Rossi, T.; Biondi, S.; Contini, S.; Thomas, R. J.; Marchioro, C. J. Am. Chem. Soc. 1995, 117, 9604.
9. Ghiron, C.; Piga, E.; Rossi, T.; Tamburini B.; Thomas, R. J. Tetrahedron Lett. 1996, 37, 3891.
10. Kennedy, G.; Rossi, T.; Tamburini, B. Tetrahedron Lett. 1996, 37, 7441.
11. Hanessian, S.; Rozema M. J. J. Am. Chem. Soc. 1996, 118, 9884.
12. Evans D. A.; Rieger, D. L.; Bilodeau, M. T.; Urpi, F. J. Am. Chem. Soc. 1991, 113, 2047.
13. (a) Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F.; Ponzini, F. J. Org. Chem. 1993, 58, 4746.
14. (b) Cinquini, M.; Cozzi, F.; Cozzi, P. G.; Consolandi, E. Tetrahedron 1991, 47, 8767.
15. Reetz, M. T.; Kesseler, K.; Schimdtberger, S.; Wenderoth, B.; Steinbach, R. Angew. Chem., Int. Ed. Engl. 1983, 22, 989.
16. Stead, P.; Marley H.; Mahmoudian, M.; Webb, G.; Noble, D.; Ip, Y. T.; Piga, E.; Rossi, T.; Roberts, S.; Dawson, M. J. Tetrahedron Asymmetry 1996, 7 (8), 2347.
17. Conformational studies on 2-methoxycyclohexanone have already been published, see: (a) Fraser, R. R.; Faibish, N. C. Can. J. Chem. 1995, 73, 88. (b) Basso, E.; Kaiser, C.; Rittner, R.; Lambert, J. B. J. Org. Chem. 1993, 58, 7865.
18. Conformational studies on 2-methoxycyclohexanone have already been published, see: (a) Fraser, R. R.; Faibish, N. C. Can. J. Chem. 1995, 73, 88. (b) Basso, E.; Kaiser, C.; Rittner, R.; Lambert, J. B. J. Org. Chem. 1993, 58, 7865.
19. (a) Reetz, M. T.; Harms, K.; Reif, W. Tetrahedron Lett. 1987, 28, 4515.
20. (b) Reetz, M. T. Acc. Chem. Res. 1993, 26, 462.
21. Denmark S. E.; Almstead, N. G. J. Am. Chem. Soc. 1993, 115, 3133.
22. Keck, G. E.; Castellino, S. J. Am. Chem. Soc. 1986, 108, 3847.