Joerg Habermann

Synthesis of an array of potential matrix metalloproteinase inhibitors using a sequence of polymer-supported reagents

Polymer-supported reagents and sequestering agents may be used to generate an array of variously substituted hydroxamic acid derivatives as potential inhibitors of matrix metalloproteinases without any chromatographic purification step.

Synthesis of the potent analgesic compound (±)-epibatidine using an orchestrated multi-step sequence of polymer supported reagents

A ten-step synthesis of (±)-epibatidine 1 is described, using an organised array of polymer supported reagents and sequestering agents in a successive manner. No chromatographic purification steps are required to afford the product in >90% purity.

Discovery of pentacyclic compounds as potent inhibitors of hepatitis C virus NS5B RNA polymerase

We report a new series of inhibitors for hepatitis C virus NS5B RNA polymerase containing a constrained pentacyclic scaffold. Our SAR studies led to the identification of hexahydroindolo[2,1-a]pyrrolo[3,2-d][2]benzazepines exposing basic groups. The compounds displayed a high activity in the enzyme assay and displayed good activity in the cell-based (replicon) assay in the presence of serum proteins.

Three-step synthesis of an array of substituted benzofurans using polymer-supported reagents

An efficient combinatorial route to substituted 3-phenylbenzofurans, is achieved by the bromination of acetophenones to α-bromoacetophenones by polymer-supported pyridinium bromide perbromide (PSPBP). The subsequent clean substitution of the obtained bromides by phenols using 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD-P) and cyclodehydration of the resulting α-phenoxyacetophenones using Amberlyst 15, affords pure products without the need for any chromatographic purification step.

Clean five-step synthesis of an array of 1,2,3,4-tetra-substituted pyrroles using polymer-supported reagents

Polymer-supported reagents and other solid sequestering agents may be used to generate an array of 1,2,3,4-tetra-substituted pyrrole derivatives without any chromato-graphic purification step.