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dc.contributor.authorHayes, Christopher J
dc.contributor.authorPalframan, Matthew J
dc.contributor.authorPattenden, Gerald
dc.date.accessioned2020-08-28T08:18:11Z
dc.date.available2020-08-28T08:18:11Z
dc.date.issued2020-02-26
dc.identifier.citationHayes, C. J., Palframan, M. J. and Pattenden, G. (2020) The impact of macrocycle conformation on the taxadiene-forming carbocation cascade: insight gained from sobralene, a recently discovered verticillene isomer, Journal of Organic Chemistry, 85 (6), pp. 4507–4514. DOI: 10.1021/acs.joc.0c00369en
dc.identifier.issn0022-3263en
dc.identifier.pmid32101002 (pubmed)
dc.identifier.doi10.1021/acs.joc.0c00369en
dc.identifier.urihttp://hdl.handle.net/2436/623534
dc.descriptionThis is an accepted manuscript of an article published by American Chemical Society in Journal of Organic Chemistry on 26/02/2020, available online: https://doi.org/10.1021/acs.joc.0c00369 The accepted version of the publication may differ from the final published version.en
dc.description.abstractCopyright © 2020 American Chemical Society. DFT calculations on the carbocation intermediates that connect the biosynthetic pathways leading to the sand fly pheromone sobralene and taxadiene have been made. Establishment of the conformation of the macrocyclic carbocation intermediate required to produce the (Z)-C8,C9 alkene bond in sobralene has identified new conformations of the verticillyl carbocation intermediates on the taxadiene biosynthetic pathway. These "sobralene-like" carbocation conformations provide an exothermic pathway to taxadiene and are validated by comparison to closely related structures (X-ray and NMR).en
dc.description.sponsorshipThe University of Nottinghamen
dc.formatapplication/pdfen
dc.languageeng
dc.language.isoenen
dc.publisherAmerican Chemical Society (ACS)en
dc.relation.urlhttps://pubs.acs.org/doi/10.1021/acs.joc.0c00369en
dc.subjectchemical structureen
dc.subjectconformationen
dc.subjectenergyen
dc.subjectmolecular structureen
dc.subjectchemical calculationsen
dc.titleThe impact of macrocycle conformation on the taxadiene-forming carbocation cascade: insight gained from sobralene, a recently discovered verticillene isomeren
dc.typeJournal articleen
dc.identifier.eissn1520-6904
dc.identifier.journalJournal of Organic Chemistryen
dc.date.updated2020-08-24T08:51:56Z
dc.contributor.institutionSchool of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, U.K.
pubs.place-of-publicationUnited States
dc.date.accepted2020-02-13
rioxxterms.funderUniversity of Nottinghamen
rioxxterms.identifier.projectUOW27082020MPen
rioxxterms.versionAMen
rioxxterms.licenseref.urihttps://creativecommons.org/licenses/by-nc-nd/4.0/en
rioxxterms.licenseref.startdate2021-02-26en
dc.source.volume85
dc.source.issue6
dc.source.beginpage4507
dc.source.endpage4514
dc.description.versionPublished version
refterms.dateFCD2020-08-27T12:44:11Z
refterms.versionFCDAM


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