Synlett 2014; 25(2): 261-264
DOI: 10.1055/s-0033-1340078
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© Georg Thieme Verlag Stuttgart · New York

Synthesis of the Anti-Melanogenic Glycerol Fatty Acid Ester Isolated from the Tuber-Barks of Colocasia antiquorum var. esculenta

Shijun Zhu
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China   Email: yikangwu@sioc.ac.cn
,
Yikang Wu*
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China   Email: yikangwu@sioc.ac.cn
› Author Affiliations
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Publication History

Received: 05 September 2013

Accepted after revision: 02 October 2013

Publication Date:
08 November 2013 (online)


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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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