David A. Muthard

An efficient synthesis of 2-substituted-thio-6-hydroxyethyl-penem-3-carboxylic acids via 2-thioxopenams

Abstract Allyl and p -nitrobenzyl (5R, 6S)-6-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-2-thioxopenam-3-carboxylates ( 19 ) were synthesized by base mediated cyclization of the corresponding 1-carboxylmethyl-4-phenoxy (thiocarbonyl)thio-2-azetidinones ( 16 ). The thioxopenams underwent alkylation and Michael reactions to produce 2-alkylthio- and 2-alkenylthio-penem derivatives 20 and 21 .

2-Naphthylcarbapenems: Broad spectrum antibiotics with enhanced potency against MRSA

A regioisomeric set of 2-naphthylcarbapenems featuring cationic substituents was synthesized. Optimal placement of the cationic group was found to markedly improve activity against methicillin-resistant staphylococci while maintaining a good spectrum of gram-negative activity.

The discovery and synthesis of 2-biphenylcarbapenems active against methicillin resistant staphylococci

Abstract The discovery and synthesis of the arylcarbapenem 2b possessing potent activity against highly resistant strains of methicillin resistant staphylococci are dislosed.

The synthesis and antibacterial activity of 2-para-quarternary ammoniomethylphenyl-carbapenems.

Abstract The synthesis and in vitro antibacterial activity of 2-phenylcarbapenems bearing a spacer linked heteroaromatic or heterocyclic quaternized moiety are discussed. In general, this class of antibiotics was found to possess antibacterial activity superior to the parent natural product, thienamycin, except for Ps. aeruginosa , and were less susceptible to degradation by the DHP-I enzyme.