Dieter Habich

Synthesis of a new carbapenem with a 6-methyl hydroxyacetate side chain

Abstract The synthesis of the 2-(4-pyridinylthio)-carbapen-2-em-3-carboxylic acid 1b , bearing a 6-methyl hydroxyacetate side chain, is described.

Straightforward Syntheses of Furanomycin Derivatives and their Biological Evaluation

Several types of furanomycin analogues were synthesized and investigated with respect to their antibacterial activity. Two different synthetic pathways were developed, based on aldol reactions/ring closing metathesis and an ester enolate Claisen rearrangement. Only the natural product and its desmethyl derivative showed antibacterial activity, pointing towards a narrow structure-activity relationship.

A short synthesis of (±) 7-oxo-3-oxa-1-azabicyclo[3.2.0] heptane-2-carboxylic acid.

Abstract A short 4-step synthesis of the title compound 3 , an inhibitor of β-lactamases, is presented. The essential step utilizes the palladium(O)-catalyzed deprotection of an allyl ester.

A novel peptide aldehyde with activity against human cytomegalovirus in two different in vivo models.

Novel peptide aldehydes (PAs) were identified as potent inhibitors of human cytomegalovirus (HCMV) in vitro. Although these compounds were highly effective against HCMV, they did not exhibit any activity against murine cytomegalovirus (MCMV). The purpose of this study was to test the antiviral activity of PA 8 as a representative of this novel class of inhibitors against HCMV in vivo. Because of the strict species specificity of HCMV we had to use two artificial animal models. In the first model, HCMV-infected human cells were entrapped into agarose plugs and transplanted into mice. In the second model, SCID mice were transplanted with human tissues that were subsequently infected with a clinical isolate of HCMV. In these two models the antiviral activity of PA 8 was clearly demonstrated, ganciclovir only being slightly superior in its in vivo antiviral activity.

Synthetic studies towards bottromycin

Summary Thio-Ugi reactions are described as an excellent synthetic tool for the synthesis of sterically highly hindered endothiopeptides. S-Methylation and subsequent amidine formation can be carried out in an inter- as well as in an intramolecular fashion. The intramolecular approach allows the synthesis of the bottromycin ring system in a straightforward manner.