Identification and total synthesis of a novel dimethylated fatty acid from the Caribbean sponge Calyx podatypa.

The dimethylated fatty acid 9,13-dimethyltetradecanoic acid was identified for the first time in nature in the Caribbean sponge Calyx podatypa where it occurs together with the rare 10, 13-dimethyltetradecanoic acid. The characterization of the novel compound was accomplished using GC-MS, pyrrolidide derivatization, and a five-step total synthesis starting with 8-bromooctanoic acid. The first racemic total synthesis for the rare 10, 13-dimethyltetradecanoic acid is also described.