Recent Advances in the Stereocontrolled Synthesis of Bi- and Tricyclic--Lactams with Non-Classical Structure

Authors: Alcaide B.; Almendros P.

Source: Current Organic Chemistry, Volume 6, Number 3, March 2002 , pp. 245-264(20)

Publisher: Bentham Science Publishers

Abstract:

-Lactams (2-azetidinones) are one crucial structural element of the natural products with antibiotic properties. Since the introduction of penicillin into therapy, bacteria have developed an incredible and growing resistance to -lactam antibiotics, essentially due to the hydrolytic ability of extremely active -lactamases. The resistance of bacteria to the classical -lactam antibiotics like penicillin and cephalosporin can be overcome, e.g., by using novel -lactam moieties in drugs which show much higher stability towards these resistance bacteria. Furthermore, the recent discoveries of some azetidine-2-ones which display a broad range of enzyme-inhibitory activity justify a renewed interest in these compounds. Besides their significance as bioactive agents, the importance of -lactams as synthetic intermediates have been widely recognized in organic synthesis. The 2-azetidinone skeleton has been extensively used as a template on which to build the carbo(hetero)cyclic structure fused to the four-membered ring, using the chirality and functionalization of the -lactam ring as a stereocontrolling element. The present review will draw special attention to radical reactions, cycloaddition reactions (Diels-Alder, [2 + 2] cycloaddition reaction, and 1,3-dipolar cycloaddition), and transition metal-catalyzed reactions (Pauson-Khand reaction, ring closing metathesis and Pd-catalyzed cyclizations) as useful methods for the preparation of bi- and tricyclic--lactams with non-classical structure.

Keywords: penicil lins; cephalosporins; amoxicillin; trinems; reverse-cope elimination; cycloaddition reactions; dipolar cycloaddition reactions; diels-alder reaction; cycloaddition reactions

Language: English

Document Type: Review article

DOI: http://dx.doi.org/10.2174/1385272024605050

Publication date: 2002-03-01

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• In this Subject: Organic Chemistry
• By this author: Alcaide B. ;  Almendros P.

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