A CONVENIENT SYNTHESIS OF PSEUDOCERATIDINE AND 3 ANALOGS FOR BIOLOGICAL EVALUATION

The recently isolated marine natural product pseudoceratidine (1) has been synthesized from 2-trichloroacetylpyrrole. Bromination in the 4- and 5-position followed by nucleophilic displacement of the trichlorom ethyl group with spermidine gave 1 in 79% yield. The procedure is gene ral and can easily be adopted to the preparation of other derivatives. This was demonstrated by the synthesis of a 5,5'-didebromo derivative (2) and two analogs (3-4). The compounds 1-4 have been tested for ant ibacterial activity and the results compared to a previous study. Also activity against the marine brine shrimp Artemia salina is reported. (C) 1997, Elsevier Science Ltd.