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Issue 12, 2014
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Synthesis of tsetse fly attractants from a cashew nut shell extract by isomerising metathesis

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Abstract

Starting from a purified cashew nut shell extract containing mostly anacardic acid derivatives, the tsetse fly attractants 3-ethyl- and 3-propylphenol were selectively synthesised. The mixture was first converted into 3-(non-8-enyl)phenol in 98% purity via ethenolysis and distillation with concomitant decarboxylation. The olefinic side chain was then shortened by isomerising cross-metathesis with short-chain olefins in the presence of a [Pd(μ-Br)(tBu3P)]2 isomerisation catalyst and a second-generation Hoveyda–Grubbs catalyst, and the synthesis was completed by a hydrogenation step.

Graphical abstract: Synthesis of tsetse fly attractants from a cashew nut shell extract by isomerising metathesis

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Supplementary files

Article information


Submitted
07 Jul 2014
Accepted
27 Aug 2014
First published
27 Aug 2014

This article is Open Access

Green Chem., 2014,16, 4885-4890
Article type
Paper
Author version available

Synthesis of tsetse fly attractants from a cashew nut shell extract by isomerising metathesis

S. Baader, P. E. Podsiadly, D. J. Cole-Hamilton and L. J. Goossen, Green Chem., 2014, 16, 4885
DOI: 10.1039/C4GC01269K

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