Synthesis of tsetse fly attractants from a cashew nut shell extract by isomerising metathesis
Synthesis of tsetse fly attractants from a cashew nut shell extract by isomerising metathesis
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DOI：
10.1039/c4gc01269k
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发表时间：
2014-01-01
期刊：
影响因子：
9.8
通讯作者：
Goossen, L. J.
中科院分区：
文献类型：
--
作者：
Baader, S.;Podsiadly, P. E.;Goossen, L. J.
以主要含有漆树酸衍生物的纯化腰果壳提取物为原料，选择性合成了采采蝇引诱剂 3-乙基-和 3-丙基苯酚。该混合物首先通过乙烯醇分解和蒸馏以及伴随的脱羧作用转化为纯度为 98% 的 3-(非 8-烯基) 苯酚。然后在[Pd(mu-Br)((Bu3P)-Bu-t)](2)异构化催化剂和第二代Hoveyda-Grubbs催化剂存在下，通过与短链烯烃的异构交叉复分解来缩短烯属侧链，并通过加氢步骤完成合成。
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(mu-Br)((Bu3P)-Bu-t)](2) isomerisation catalyst and a second-generation Hoveyda-Grubbs catalyst, and the synthesis was completed by a hydrogenation step.