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Syntheses of combretastatins D-1, D-2, and D-4 via ring contraction by flash vacuum pyrolysis

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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.identifier248138936
dc.identifier96846004-9ed8-442b-a804-2d64f003fa2f
dc.identifier85018462191
dc.identifier000391781900055
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 ' , The 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.otherORCID: /0000-0001-6959-5311/work/34857566
dc.identifier.urihttps://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.format.extent910312
dc.language.isoeng
dc.relation.ispartofThe Journal of Organic Chemistryen
dc.subjectQD Chemistryen
dc.subjectNDASen
dc.subjectBDCen
dc.subjectR2Cen
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.contributor.institutionUniversity of St Andrews. EaSTCHEMen
dc.contributor.institutionUniversity of St Andrews. School of Chemistryen
dc.identifier.doi10.1021/acs.joc.6b02586
dc.description.statusPeer revieweden
dc.date.embargoedUntil2017-12-07


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