Stereoselective synthesis of optically active beta-lactams, potential inhibitors of pilus assembly in pathogenic bacteria.
[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.
Emtenäs
H
H
Organic Chemistry, Umeâ University, S-901 87 Umeâ, Sweden.
Soto
G
G
Hultgren
S J
SJ
Marshall
G R
GR
Almqvist
F
F
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D001419:Bacteria / Q000187:drug effects* / Q000378:metabolism; D018360:Crystallography, X-Ray; D010861:Fimbriae, Bacterial / Q000187:drug effects*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D013237:Stereoisomerism; D047090:beta-Lactams
D000900:Anti-Bacterial Agents; D047090:beta-Lactams