Total synthesis and stereochemical reassignment of tasiamide

The total synthesis of a marine acyclic peptide tasiamide and three diastereomers was reported for the first time. The synthesis has led to a reassignment of the Nα-Me-L-Gln of tasiamide to be Nα-Me-D-Gln, which was supported by 1H NMR, 13C NMR, COSY, HMQC, HMBC, and optical rotation. Copyright © 2008 European Peptide Society and John Wiley & Sons, Ltd.