Synthesis of tsetse fly attractants from a cashew nut shell extract by isomerising metathesis
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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.
Baader , S , Podsiadly , P E , Cole-Hamilton , D J & Goossen , L J 2014 , ' Synthesis of tsetse fly attractants from a cashew nut shell extract by isomerising metathesis ' Green Chemistry , vol. 16 , no. 12 , pp. 4885-4890 . DOI: 10.1039/c4gc01269k
© Authors 2014. This Open Access Article is licensed under a Creative Commons Attribution-Non Commercial 3.0 Unported Licence (http://creativecommons.org/licenses/by-nc/3.0/)
DescriptionThe authors thank NanoKat, the Collaborative Research Centre SFB/TRR 88 “3MET”, Carl Zeiss (RCR) and the Deutsche Bundesstiftung Umwelt (fellowship to S.B.) for financial support.
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