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dc.contributor.authorShi, Yiping
dc.contributor.authorKamer, Paul C. J.
dc.contributor.authorCole-Hamilton, David J.
dc.date.accessioned2019-03-22T12:30:08Z
dc.date.available2019-03-22T12:30:08Z
dc.date.issued2019-03-07
dc.identifier.citationShi , Y , Kamer , P C J & Cole-Hamilton , D J 2019 , ' Synthesis of pharmaceutical drugs from cardanol derived from cashew nut shell liquid ' , Green Chemistry , vol. 21 , no. 5 , pp. 1043-1053 . https://doi.org/10.1039/C8GC03823Fen
dc.identifier.issn1463-9262
dc.identifier.otherPURE: 258270851
dc.identifier.otherPURE UUID: 4a837700-48dd-4d8e-9f2c-f5d18a6d7799
dc.identifier.otherRIS: urn:C6C6D4C77B28CED33399BEBE82738CAD
dc.identifier.otherScopus: 85062547030
dc.identifier.otherWOS: 000461723200012
dc.identifier.urihttp://hdl.handle.net/10023/17347
dc.descriptionAuthors thank the EPSRC for the critical mass grant ‘Clean Catalysis for Sustainable Development’ (EP/J018139/1), Sasol Technology, UK for a case studentship (Y. S.).en
dc.description.abstractCardanol from cashew nut shell liquid extracted from cashew nut shells was successfully converted into various useful pharmaceutical drugs, such as norfenefrine, rac-phenylephrine, etilefrine and fenoprofene. 3-Vinylphenol, the key intermediate for the synthesis of these drugs, was synthesised from cardanol by ethenolysis to 3-non-8-enylphenol followed by isomerising ethenolysis. The metathesis reaction worked very well using DCM, but the greener solvent, 2-methyl tetrahydrofuran, also gave very similar results. Hydroxyamination of 3-vinylphenol with an iron porphyrin catalyst afforded norfenefrine in over 70% yield. Methylation and ethylation of norfenefrine afforded rac-phenylephrine and etilefrine respectively. A sequence of C–O coupling, isomerising metathesis and selective methoxycarbonylation afforded fenoprofene in good yield. A comparison of the routes described in this paper with some standard literature syntheses of 3-vinylphenol and of the drug molecules shows significant environmental advantages in terms of precursors, yields, number of steps, conditions and the use of catalysts. The Atom Economy of our processes is generally similar or significantly superior to those of the literature processes mainly because the side products produced during synthesis of 3-vinylphenol (1-octeme, 1,4-cyclohexadiene and propene) are easily separable and of commercial value, especially as they are bio-derived. The E Factor for the production of 2-vinylphenol by our process is also very low compared with those of previously reported syntheses.
dc.format.extent11
dc.language.isoeng
dc.relation.ispartofGreen Chemistryen
dc.rightsCopyright © 2019 The Author(s). Open Access article. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.en
dc.subjectQD Chemistryen
dc.subjectRM Therapeutics. Pharmacologyen
dc.subjectNDASen
dc.subject.lccQDen
dc.subject.lccRMen
dc.titleSynthesis of pharmaceutical drugs from cardanol derived from cashew nut shell liquiden
dc.typeJournal articleen
dc.description.versionPublisher PDFen
dc.contributor.institutionUniversity of St Andrews.School of Chemistryen
dc.identifier.doihttps://doi.org/10.1039/C8GC03823F
dc.description.statusPeer revieweden


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