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dc.contributor.authorHealy, A.R.
dc.contributor.authorVinale, F.
dc.contributor.authorLorito, M.
dc.contributor.authorWestwood, Nicholas James
dc.date.accessioned2015-03-11T17:01:02Z
dc.date.available2015-03-11T17:01:02Z
dc.date.issued2015-02-06
dc.identifier.citationHealy , A R , Vinale , F , Lorito , M & Westwood , N J 2015 , ' Total synthesis and biological evaluation of the tetramic acid based natural product harzianic acid and its stereoisomers ' , Organic Letters , vol. 17 , no. 3 , pp. 692-695 . https://doi.org/10.1021/ol503717ren
dc.identifier.issn1523-7060
dc.identifier.otherPURE: 170635216
dc.identifier.otherPURE UUID: 0429d76e-7f41-40c6-8f59-60cb922244a0
dc.identifier.otherScopus: 84922604127
dc.identifier.otherORCID: /0000-0003-0630-0138/work/56424176
dc.identifier.otherWOS: 000349274200076
dc.identifier.urihttps://hdl.handle.net/10023/6207
dc.descriptionFinancial support for this project was provided by Cancer Research UK (Grant No. C21383/A6950)en
dc.description.abstractThe bioactive natural product harzianic acid was prepared for the first time in just six steps (longest linear sequence) with an overall yield of 22%. The identification of conditions to telescope amide bond formation and a Lacey-Dieckmann reaction into one pot proved important. The three stereoisomers of harzianic acid were also prepared, providing material for comparison of their biological activity. While all of the isomers promoted root growth, improved antifungal activity was unexpectedly associated with isomers in the enantiomeric series opposite that of harzianic acid.
dc.format.extent4
dc.language.isoeng
dc.relation.ispartofOrganic Lettersen
dc.rights© 2015 American Chemical Society. This is an open access article published under a Creative Commons Attribution (CC-BY) License, which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.en
dc.subjectQD Chemistryen
dc.subjectDASen
dc.subject.lccQDen
dc.titleTotal synthesis and biological evaluation of the tetramic acid based natural product harzianic acid and its stereoisomersen
dc.typeJournal articleen
dc.description.versionPublisher PDFen
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.identifier.doihttps://doi.org/10.1021/ol503717r
dc.description.statusPeer revieweden


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