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The Synthesis of Penem Antibiotics

Author: ZhaoZuo
Tutor: ZhangWenJun
School: Hebei University of Technology
Course: Applied Chemistry
Keywords: antibiotics penem 4AA synthesis
CLC: TQ465.1
Type: Master's thesis
Year: 2009
Downloads: 150
Quote: 1
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Abstract


The structure of penem is similar to the combination of the thiazolidine ring in penicillin a- nd the dihydrothiazine ring in cephalosporins. Penem show broad-spectrum antibacterial activity against both aerobic and anaerobic Gram-positive and Gram-negative bacteria and it is absorbed easily. An important property of penem is their resistance to the actions ofβ-lactamases and DHP -Ⅰ.Mulriple structures and new penem antibiotics are required exigently because of the inferior stability and low activity against Pseudomonas aeruginosa. We designed and synthesized a series of penems with 2-phenyl and 2-phenylethylene.Our research was focused on the synthesis of new penem compounds. Displacement of the acetoxy group of the optical activity material (3R,4R)-3-[(1R)-tert-butyldimethylsilyloxyethyl]- 4-acetoxy-2-azetidinone (4AA) with the thionocarboxylic acids, acylation to provide the oxalam- ide, followed by triethylphosphite-induced cyclization to afford the target compounds. 7 compo- unds and intermediates were synthesized, of which 5 compounds were previously unreported. All the compounds were verified by MS, NMR and other methods.

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CLC: > Industrial Technology > Chemical Industry > Pharmaceutical chemical industry > Antibiotics manufacture > Penicillin and its derivatives
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