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 trichloromethyl group with spermidine gave 1 in 79% yield. The procedure is general 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 antibacterial activity and the results compared to a previous study. Also activity against the marine brine shrimp Artemia salina is reported.
|Journal||Bioorganic & Medicinal Chemistry Letters|
|Publication status||Published - 1997|
Behrens, C., Christoffersen, M. W., Gram, L., & Nielsen, P. H. (1997). A convenient synthesis of pseudoceratidine and three analogs for biological evaluation. Bioorganic & Medicinal Chemistry Letters, 7(3), 321-326.