Total synthesis and stereochemical reassignment of tasiamide B

The first total synthesis of tasiamide B, an octapeptide bearing 4-amino-3-hydroxy-5-phenylpentanoic acid unit isolated from the marine cyanobacteria Symploca sp. is described. A simple and efficient way was found to avoid the pyroglutamylation of N-alpha-Me-Gln and led to a reassignment of the N-alpha-Me-L-Phe of tasiamide B to be N-alpha-Me-D-Phe, which was also supported by 1D and 2D NMR. Copyright (C) 2010 European Peptide Society and John Wiley & Sons, Ltd.