Synthesis of the marine natural product barbamide

The first total synthesis of the trichlorinated natural product barbamide i s described. The convergent approach involves coupling (S)-3-trichloromethy lbutanoyl chloride with Meldrum's acid (2,2-dimethyl-1,3-dioxane-4,6-dione) to give 15 followed by addition of the novel secondary amine N-methyl-(S)- dolaphenine 2 (prepared in 6 steps and 24% overall yield from N-CbZ-L-pheny lalanine) to give the beta -keto amide 16 which was converted directly to t he required (E)enol ether.