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Stereoselective Synthesis of Optically Active β-Lactams, Potential Inhibitors of Pilus Assembly in Pathogenic Bacteria

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journal contribution
posted on 20.06.2000, 00:00 by Hans Emtenäs, Gabe Soto, Scott J. Hultgren, Garland R. Marshall, Fredrik Almqvist
Optically active β-lactams 3 are obtained in excellent yields (up to 93%) and with complete stereoselectivity from Meldrum's acid derivatives 1 and Δ2-thiazolines 2. A selective reduction to aldehydes 5 (R = Ar or CH2Ar) was then accomplished by using DIBAL-H. This rigid framework, with stereochemistry different than that of penicillin, is designed to be a suitable scaffold for the development of compounds inhibiting pilus formation in uropathogenic Escherichia coli.