Synthesis of Methyl (5Z,9Z,17R)-17-Methylnonadeca-5,9-dienoate, the (R)-Enantiomer of the Structure Proposed for a Metabolite of the Philippine Sponge Plakinastrella sp.

Miho TAKAGI; Hirosato TAKIKAWA; Kenji MORI

doi:10.1271/bbb.65.2065

Organic Chemistry

Synthesis of Methyl (5Z,9Z,17R)-17-Methylnonadeca-5,9-dienoate, the (R)-Enantiomer of the Structure Proposed for a Metabolite of the Philippine Sponge Plakinastrella sp.

Miho TAKAGI, Hirosato TAKIKAWA, Kenji MORI

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Keywords: marine natural product, methyl-branched fatty acid, optically active fatty acid, Plakinastrella sp., sponge

JOURNAL FREE ACCESS

2001 Volume 65 Issue 9 Pages 2065-2069

DOI https://doi.org/10.1271/bbb.65.2065

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Abstract

The (R)-enantiomer (1) of methyl (5Z,9Z)-17-methyl-nonadeca-5,9-dienoate, the structure proposed for a metabolite of the Philippine sponge, Plakinastrella sp., was synthesized. The ¹H- and ¹³C-NMR spectra of the synthetic material were different from those reported for the natural product. The proposed structure 1 is therefore incorrect.

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