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dc.contributor.authorClark, Joshua
dc.contributor.authorNeyyappadath, Rifahath M.
dc.contributor.authorYu, Cihang
dc.contributor.authorSlawin, Alexandra M. Z.
dc.contributor.authorCordes, David B.
dc.contributor.authorO'Hagan, David
dc.identifier.citationClark , J , Neyyappadath , R M , Yu , C , Slawin , A M Z , Cordes , D B & O'Hagan , D 2021 , ' Janus all- cis 2,3,4,5,6-pentafluorocyclohexyl building blocks applied to medicinal chemistry and bioactives discovery chemistry ' , Chemistry - A European Journal , vol. 27 , no. 64 , 202102819 , pp. 16000-16005 .
dc.identifier.otherPURE: 275759219
dc.identifier.otherPURE UUID: 3eb00041-ec0a-4aa9-823b-4397ad369478
dc.identifier.otherRIS: urn:222867F1684BC4E4C2572CF96C419D0D
dc.identifier.otherORCID: /0000-0002-0510-5552/work/101217835
dc.identifier.otherORCID: /0000-0002-9527-6418/work/101217853
dc.identifier.otherORCID: /0000-0002-5366-9168/work/101217884
dc.identifier.otherScopus: 85116415558
dc.identifier.otherWOS: 000703997000001
dc.descriptionWe thank EPSRC for a grant (EP/R013799/1) and Studentships (JLC) through the EPSRC CRITICAT CDT programme and also the Chinese Scholarship Council (CY).en
dc.description.abstractMonoalkylated derivatives of the unusually polar all- cis 2,3,4,5,6- pentafluorocyclohexyl (Janus face) motif are prepared starting from an aryl hydrogenation of 2,3,4,5,6- pentafluorophenylacetate methyl ester 15 . The method used Zeng's Rh(CAAC) carbene catalyst 4 in the hydrogenation following the protocol developed by Glorius. The resultant Janus pentafluorocyclohexylacetate methyl ester 16 was converted to the corresponding alcohol 18 , aldehyde 13 , bromide 29 and azide 14 through functional group manipulations, and some of these building blocks were used in Ugi-multicomponent and Cu-catalysed click reactions. NBoc protected pentafluoroarylphenylalanine methyl ester 35 was also subject to an aryl hydrogenation, and then deprotection to generate the Janus face ß-pentafluorocyclohexyl-alanine amino acid 15 , which was incorporated into representative members of an emerging class of candidate antiviral compounds. Log P measurements demonstrate that the all- cis 2,3,4,5,6-pentafluorocyclohexyl ring system is more polar than a phenyl ring. In overview the paper introduces new building blocks containing this Janus ring and demonstrates their progression to molecules typically used in bioactives discovery programmes.
dc.relation.ispartofChemistry - A European Journalen
dc.rightsCopyright © 2021 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.en
dc.subjectOrganofluorine chemistryen
dc.subjectJanus motifen
dc.subjectAryl hydrogenationen
dc.subjectOrganic chemistryen
dc.subjectQD Chemistryen
dc.subjectQH301 Biologyen
dc.subjectR Medicineen
dc.titleJanus all-cis 2,3,4,5,6-pentafluorocyclohexyl building blocks applied to medicinal chemistry and bioactives discovery chemistryen
dc.typeJournal articleen
dc.description.versionPublisher PDFen
dc.contributor.institutionUniversity of St Andrews. School of Chemistryen
dc.contributor.institutionUniversity of St Andrews. Biomedical Sciences Research Complexen
dc.contributor.institutionUniversity of St Andrews. EaSTCHEMen
dc.description.statusPeer revieweden

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