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Royal Society of Chemistry, Green Chemistry, 12(16), p. 4885-4890

DOI: 10.1039/c4gc01269k

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Synthesis of Tsetse Fly Attractants from a Cashew Nut Shell Extract by Isomerising Metathesis

This paper is made freely available by the publisher.
This paper is made freely available by the publisher.

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Abstract

Starting from a purified cashew nut shell extract containing mostly anacardic acid derivatives, the tsetse fly attractant 3-propylphenol was 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.