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

S. Baader*, P. E. Podsiadly, D. J. Cole-Hamilton, L. J. Goossen

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

36 Citations (Scopus)
2 Downloads (Pure)

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.

Original languageEnglish
Pages (from-to)4885-4890
Number of pages6
JournalGreen Chemistry
Volume16
Issue number12
Early online date27 Aug 2014
DOIs
Publication statusPublished - 1 Dec 2014

Keywords

  • Olefin metathesis
  • Carboxylic-acids
  • Sleeping sickness
  • Methyl oleate
  • Buffalo urine
  • Ethenolysis
  • Catalysts
  • Cardanol
  • Liquid
  • Chemicals

Fingerprint

Dive into the research topics of 'Synthesis of tsetse fly attractants from a cashew nut shell extract by isomerising metathesis'. Together they form a unique fingerprint.

Cite this