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

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 viaethenolysis and distillation with concomitan...

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Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2014-01, Vol.16 (12), p.4885-4890
Main Authors: Baader, S, Podsiadly, P E, Cole-Hamilton, D J, Goossen, L J
Format: Article
Language:English
Subjects:
Anacardium
Catalysts
Chains
Decarboxylation
Derivatives
Glossina
Hydrogenation
Isomerization
Olefins
Synthesis
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Summary: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 viaethenolysis 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( mu -Br)( super(t)Bu sub(3)P)] sub(2) isomerisation catalyst and a second-generation Hoveyda-Grubbs catalyst, and the synthesis was completed by a hydrogenation step.
ISSN:1463-9262
1463-9270
DOI:10.1039/c4gc01269k