Synthesis of the marine natural product barbamide.
The first total synthesis of the trichlorinated natural product barbamide is described. The convergent approach involves coupling (S)-3-trichloromethylbutanoyl 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-phenylalanine) to give the beta-keto amide 16 which was converted directly to the required (E)-enol ether.
Nguyen
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VA
School of Chemistry, University of Bristol, Cantock's Close, Bristol, UK BS8 1TS.
Willis
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Gerwick
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D000458:Cyanobacteria / Q000737:chemistry; D019015:Geologic Sediments / Q000382:microbiology*; D010456:Peptides, Cyclic / Q000737:chemistry; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry
D010456:Peptides, Cyclic; D013844:Thiazoles; C100545:barbamide