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.
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Department of Chemistry, University of Puerto Rico, P.O. Box 23346, San Juan, Puerto Rico 00931, USA. ncarball@upracd.upr.clu.edu
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D000818:Animals; D002849:Chromatography, Gas; D005227:Fatty Acids / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D011161:Porifera / Q000737:chemistry*; D017550:Spectroscopy, Fourier Transform Infrared
C411203:10,13-dimethyltetradecanoic acid; C411202:9,13-dimethyltetradecanoic acid; D005227:Fatty Acids