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dc.contributor.authorHarras, Marina
dc.contributor.authorMilius, Wolfgang
dc.contributor.authorAitken, R Alan
dc.contributor.authorSchobert, Rainer
dc.date.accessioned2017-12-08T00:32:01Z
dc.date.available2017-12-08T00:32:01Z
dc.date.issued2017-01-06
dc.identifier.citationHarras , M , Milius , W , Aitken , R A & Schobert , R 2017 , ' Syntheses of combretastatins D-1, D-2, and D-4 via ring contraction by flash vacuum pyrolysis ' , Journal of Organic Chemistry , vol. 82 , no. 1 , pp. 579-587 . https://doi.org/10.1021/acs.joc.6b02586en
dc.identifier.issn0022-3263
dc.identifier.otherPURE: 248138936
dc.identifier.otherPURE UUID: 96846004-9ed8-442b-a804-2d64f003fa2f
dc.identifier.otherScopus: 85018462191
dc.identifier.otherORCID: /0000-0001-6959-5311/work/34857566
dc.identifier.otherWOS: 000391781900055
dc.identifier.urihttp://hdl.handle.net/10023/12292
dc.description.abstractWe report the syntheses of combretastatins D-2 and D-4 as well as a formal synthesis of combretastatin D-1 by a conceptually new route harnessing a ring-contracting flash vacuum pyrolytic extrusion of sulfur dioxide from the respective 16-membered sulfone precursors. Via flash vacuum pyrolysis, even metaparacyclophanes as small and strained as the hitherto unknown oxa[1.5]metaparacyclophane could be prepared as a side product en route to combretastatin D-2 by synchronous extrusion of SO2 and CO2.
dc.format.extent9
dc.language.isoeng
dc.relation.ispartofJournal of Organic Chemistryen
dc.rightsCopyright © 2016 American Chemical Society. 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 may differ slightly from the final published version. The final published version of this work is available at: https://doi.org/10.1021/acs.joc.6b02586en
dc.subjectQD Chemistryen
dc.subjectNDASen
dc.subjectBDCen
dc.subject.lccQDen
dc.titleSyntheses of combretastatins D-1, D-2, and D-4 via ring contraction by flash vacuum pyrolysisen
dc.typeJournal articleen
dc.description.versionPostprinten
dc.contributor.institutionUniversity of St Andrews.EaSTCHEMen
dc.contributor.institutionUniversity of St Andrews.School of Chemistryen
dc.identifier.doihttps://doi.org/10.1021/acs.joc.6b02586
dc.description.statusPeer revieweden
dc.date.embargoedUntil2017-12-07


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