Two approaches to the synthesis of (2
S,4
S)-5,5-dichloroleucine are compared, and the parent amino acid was used in the first total synthesisof the polychlorinated marine natural product, dysamide B. A key step was the lead tetraacetate-mediated decarboxylation of an
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,
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-dichloroacid in the presence of 1,4-cyclohexadiene to generate the dichloromethyl group.