| Abstract
| - The first biomimetic total synthesis of the iron chelator anachelin H isolated from the cyanobacteriumAnabaena cylindrica is reported. A first generation approach delivered one enantiomeric series of thepolyketide fragment. Comparison of the 1H NMR data suggested the relative configuration of this anachelinfragment. The relative and absolute configuration of anachelin H was then established by total synthesis.A second generation approach involved the enzymatic conversion of N,N-dimethyltyramine to the anachelinchromophore. It was demonstrated that the enzyme tyrosinase is activated by the product during thisreaction, the anachelin chromophore can serve as a tyrosinase activator. Anachelin H was evaluatedagainst a panel of eleven bacterial and fungal pathogens, and moderate antibiotic activity (32 μg/mL)against Moraxella catarrhalis was found.
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