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

doi:10.1039/c4gc01269k

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 journal › Article › peer-review

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 language	English
Pages (from-to)	4885-4890
Number of pages	6
Journal	Green Chemistry
Volume	16
Issue number	12
Early online date	27 Aug 2014
DOIs	https://doi.org/10.1039/c4gc01269k
Publication status	Published - 1 Dec 2014

Keywords

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

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1039/c4gc01269k

Cole_2014_GreenChem_Synthesis
© 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/)
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title = "Synthesis of tsetse fly attractants from a cashew nut shell extract by isomerising metathesis",

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.",

keywords = "Olefin metathesis, Carboxylic-acids, Sleeping sickness, Methyl oleate, Buffalo urine, Ethenolysis, Catalysts, Cardanol, Liquid, Chemicals",

author = "S. Baader and Podsiadly, {P. E.} and Cole-Hamilton, {D. J.} and Goossen, {L. J.}",

note = "The 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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T1 - Synthesis of tsetse fly attractants from a cashew nut shell extract by isomerising metathesis

AU - Baader, S.

AU - Podsiadly, P. E.

AU - Cole-Hamilton, D. J.

AU - Goossen, L. J.

N1 - The 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.

PY - 2014/12/1

Y1 - 2014/12/1

N2 - 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.

AB - 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.

KW - Olefin metathesis

KW - Carboxylic-acids

KW - Sleeping sickness

KW - Methyl oleate

KW - Buffalo urine

KW - Ethenolysis

KW - Catalysts

KW - Cardanol

KW - Liquid

KW - Chemicals

UR - http://www.rsc.org/suppdata/gc/c4/c4gc01269k/c4gc01269k1.pdf

U2 - 10.1039/c4gc01269k

DO - 10.1039/c4gc01269k

M3 - Article

SN - 1463-9262

VL - 16

SP - 4885

EP - 4890

JO - Green Chemistry

JF - Green Chemistry

IS - 12

ER -

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

Abstract

Keywords

UN SDGs

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