PRACTICAL SYNTHESIS OF (3S,4R)-3-[(R)-1-(TERT-BUTYLDIMETHYLSILOXY)-ETHYL]-4-(METHYLSULFONYL)-2-AZETIDINONE FROM DIBROMOPENICILLANIC ACID S,S-DIOXIDE - A PENEM SYNTHON

ß-Lactams have intrigued chemists for decades.1The allurement has been the result of their labyrinthine chemical structure in tandem with their valuable biological activity. Woodward introduced a new dimension to β-lactam research by synthesizing the first penem and demonstrating the inherent antibacterial activity2present in this ring system. His pioneering strategy of thiazoline ring construction onto an appropriately substituted azetidinone is still the most commonly employed approach to penems.3Our penem research, as well as others, targeted 3,4-di-subtituted azetidinones as key synthons. © 1990, American Chemical Society. All rights reserved.