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dc.contributor.authorOjo, O. Stephen
dc.contributor.authorNardone, Brunello
dc.contributor.authorMusolino, Stefania Francesca
dc.contributor.authorNeal, Andrew
dc.contributor.authorWilson, Liam
dc.contributor.authorLebl, Tomas
dc.contributor.authorSlawin, Alexandra Martha Zoya
dc.contributor.authorCordes, David Bradford
dc.contributor.authorTaylor, James Edward
dc.contributor.authorNaismith, James H.
dc.contributor.authorSmith, Andrew D.
dc.contributor.authorWestwood, Nicholas J.
dc.identifier.citationOjo , O S , Nardone , B , Musolino , S F , Neal , A , Wilson , L , Lebl , T , Slawin , A M Z , Cordes , D B , Taylor , J E , Naismith , J H , Smith , A D & Westwood , N J 2018 , ' Synthesis of the natural product descurainolide and cyclic peptides from lignin-derived aromatics ' , Organic & Biomolecular Chemistry , vol. 16 , no. 2 , pp. 266-273 .
dc.identifier.otherPURE: 251752326
dc.identifier.otherPURE UUID: e576b6a5-bd08-49d0-be22-12ed9edfd2aa
dc.identifier.otherScopus: 85040222509
dc.identifier.otherORCID: /0000-0002-2104-7313/work/39933531
dc.identifier.otherORCID: /0000-0002-0269-3221/work/48131706
dc.identifier.otherORCID: /0000-0002-5366-9168/work/39933584
dc.identifier.otherORCID: /0000-0003-0630-0138/work/56424144
dc.identifier.otherORCID: /0000-0002-9527-6418/work/56861441
dc.identifier.otherWOS: 000419388500014
dc.descriptionThe authors acknowledge the EPSRC UK National Mass Spectrometry Facility at Swansea University for mass spectrometry analysis. Financial support from: the Engineering and Physical Sciences Research Council (grant EP/J018139/1, EP/K00445X/1 (NJW, ADS, OSO), the doctoral training grant (ARN) and the CRITICAT Centre for Doctoral Training [Ph.D. studentship to SFM; Grant code: EP/L016419/1]), the Leverhulme Trust (JET), European Research Council (ERC-2013-ADG (JHN))en
dc.description.abstractAlternative sources of potential feedstock chemicals are of increasing importance as the availability of oil decreases. The biopolymer lignin is viewed as a source of useful mono-aromatic compounds as exemplified by the industrial scale production of vanillin from this biomass. Alternative lignin-derived aromatics are available in pure form but to date examples of the use of these types of compounds are rare. Here we address this issue by reporting the conversion of an aromatic keto-alcohol to the anti- and syn-isomers of Descurainolide A. The key step involves a rhodium-catalyzed allylic substitution reaction. Enantioenriched allylic alcohols were generated via an isothiourea-catalyzed kinetic resolution enabling access to both the (2R,3R) and (2S,3S) enantiomers of anti-Descurainolide A. In addition we show that the ligninderived keto-alcohols can be converted into unnatural amino acid derivatives of tyrosine. Finally, these amino acids were incorporated into cyclic peptide scaffolds through the use of both chemical and an enzyme-mediated macrocylisation.
dc.relation.ispartofOrganic & Biomolecular Chemistryen
dc.rights© 2017 the Authors. This work has been made available online in accordance with the publisher’s policies. This is the author created accepted version manuscript following peer review and as such may differ slightly from the final published version. The final published version of this work is available at 10.1039/C7OB02697Hen
dc.subjectQD Chemistryen
dc.titleSynthesis of the natural product descurainolide and cyclic peptides from lignin-derived aromaticsen
dc.typeJournal articleen
dc.contributor.institutionUniversity of St Andrews.School of Chemistryen
dc.contributor.institutionUniversity of St Andrews.EaSTCHEMen
dc.contributor.institutionUniversity of St Andrews.Biomedical Sciences Research Complexen
dc.description.statusPeer revieweden

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