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Stereoselective synthesis of optically active beta-lactams, potential inhibitors of pilus assembly in pathogenic
H Emtenäs1, G Soto, S J Hultgren
1Organic Chemistry, Umeâ University, S-901 87 Umeâ, Sweden.
Organic Letters
|July 13, 2000
Abstract:
[reaction: see text] Optically active beta-lactams 3 are obtained in excellent yields (up to 93%) and with complete stereoselectivity from Meldrum's acid derivatives 1 and Delta(2)-thiazolines 2. A selective reduction to aldehydes 5 (R = Ar or CH(2)Ar) 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.