Highly Diastereoselective Synthesis of 4- N-Methylformamidino Trinem (GV129606), a Potent Antibacterial Agent

• Published in: Tetrahedron Vol. 56; no. 31; pp. 5649 - 5655
• Main Authors: Biondi, Stefano, Pecunioso, Angelo, Busi, Filippo, Contini, Stefania A, Donati, Daniele, Maffeis, Micaela, Pizzi, Domenica A, Rossi, Luciana, Rossi, Tino, Sabbatini, Fabio M
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 28-07-2000
• Subjects: diastereoselective synthesis; gram-negative bacteria; pseudomonads; trinems; β-lactams; β-lactams; gram-negative bacteria; diastereoselective synthesis; pseudomonads; trinems
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/S0040-4020(00)00414-2

In this paper a highly diastereoselective synthesis of 4-
N-methylformamidino trinem
3 is reported. The route offers advantages compared to that previously used, i.e. the higher overall yield, the robustness, the avoidance of toxic reagents. Most of the compounds were isolated by precipitation, therefore reducing the number of chromatographic separations. The efficient conversion of 4-
N-methylamino trinem
11 into GV129606
3, was obtained by a new methodology in which a scavenger resin was used. The route presented in this paper allowed the preparation of the material required for early development studies and demonstrates the versatility of cyclohexenyl azetidinone
12 in the synthesis of 4-substituted trinems.