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Issue 33, 2017
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A synthetic dodecanolide library for the identification of putative semiochemicals emitted by mantellid frogs

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Abstract

Aliphatic macrolides are used by various organisms as semiochemicals or pheromones, e.g. by the endemic Madagascan frog family Mantellinae. Volatile, methyl-branched aliphatic macrolides occur in various species, but their identification by MS is difficult, while isolation is not possible due to the low amounts produced. Therefore, we synthesized a library of methyl-branched 11-dodecanolides to identify unknown macrolides secreted by Gephyromantis moseri, a mantelline frog restricted to the rainforest and characterized by largely terrestrial habitats. The syntheses used metal-organic epoxide opening and ring-closing-metathesis as key steps. All library members 2-, 4-, 6-, 8-, and 10-methyl-11-dodecanolide were thus identified as part of the secretion by comparison of their mass spectra and their gas chromatographic retention indices. These compounds comprise new natural products.

Graphical abstract: A synthetic dodecanolide library for the identification of putative semiochemicals emitted by mantellid frogs

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Supplementary files

Article information


Submitted
05 Apr 2017
Accepted
10 Jul 2017
First published
10 Jul 2017

Org. Biomol. Chem., 2017,15, 6967-6977
Article type
Paper

A synthetic dodecanolide library for the identification of putative semiochemicals emitted by mantellid frogs

P. S. Peram, M. Vences and S. Schulz, Org. Biomol. Chem., 2017, 15, 6967
DOI: 10.1039/C7OB00849J

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