Abstract
(2′S)-1-O-9-Oxo-(10E,12E)-octadecadienoyl glycerol, a natural anti-melanogenic monoglyceride, is synthesized for the first time. The chiral pool based route employed not only confirms the absolute configuration, but also illustrates the first synthetic entry to the (E,E)-diene keto acid, which is another molecule of biological importance. The confusion caused by the misinterpreted 1H NMR spectroscopic data for the (E,E)-diene motif in the literature is discussed. The first unequivocal piece of evidence for the assigned (12E) configuration is also presented.
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