The stereoselective synthesis of a key intermediate of the trinem antibiotic Sanfetrinem

Tetrahedron Letters

Volumn 37, Issue 22, 1996, Pages 3891-3894

  Ghiron, Chiara ^a   Piga, Elisabetta ^a   Rossi, Tino ^a   Tamburini, Bruno ^a   Thomas, Russell J ^a  

^a GSK   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

SANFETRINEM;

ANTIBACTERIAL ACTIVITY; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ORAL DRUG ADMINISTRATION; STEREOCHEMISTRY;

EID: 0029936143     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00682-X     Document Type: Article

References (10)

1. Di Modugno, E; Erbetti, I.; Ferrari. L; Galassi, G; Hammond, S.H.; Xerri, L.; Antimicrob. Agents Chemother., 1994, 38, 2362.
2. For the most recent references to the synthesis of trinem GV104326 see: a) Rossi, T., Biondi, S., Contini, S., Thomas, R. J. and Marchioro C.; J. Am. Chem. Soc., 1995, 117, 9604.
3. b) Bismara, C., Donati, D., Di Fabio, R., Rossi, T., and Thomas, R. J.; Tetrahedron Lett., 1995, 36, 4283.
4. Part of this work was presented in a poster at the OMCOS8 conference, Santa Barbara, California, August 1995.
5. The only reported example of a C-nucleophile entering cis-to the hydroxyethyl side chain of compound 3 is given in reference 2a.
6. For the formation of compound 10 using LDA and TMSCl see Kowalski, C., Creary, X., Rollin, A. J. and Burke, C. M.; J. Org. Chem., 1978, 43, 2601.
7. Rossi, L. and Pecunioso, A.;Tetrahedron Lett. 1994, 35, 5285.
8. Initial experiments also indicated that under these conditions significantly improved yields and selectivity in the condensation were obtained with the N-TMS protected 11 with respect to both the unprotected 3 and the N-TBDMS derivative.
9. In a further preliminary experiment we noted that under these conditions using tin tetrachloride without ligands an extremely rapid reaction occured with a low yield of the desired compound 7a.
10. Stead, P., Rossi, T., Roberts, S. M. et al., forthcoming publication.