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Please use this identifier to cite or link to this item: https://hdl.handle.net/1959.11/22785
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dc.contributor.authorLegendre, Sarahen
dc.contributor.authorJevric, Martynen
dc.contributor.authorKlepp, Julianen
dc.contributor.authorSumby, Christopher Jen
dc.contributor.authorGreatrex, Benen
dc.date.accessioned2018-04-12T16:02:00Z-
dc.date.issued2018-
dc.identifier.citationTetrahedron, 74(12), p. 1229-1239en
dc.identifier.issn1464-5416en
dc.identifier.issn0040-4020en
dc.identifier.urihttps://hdl.handle.net/1959.11/22785-
dc.description.abstractA Kornblum-DeLaMare/aza-Michael reaction of 3,6-dihydro-1,2-dioxines with primary and secondary amines has been developed which affords 4-hydroxy-3-aminoketones. The aza-Michael products were reduced using non-selective NaBH4/MeOH or diastereoselective (up to 92:8) SnCl4/NaBH4 conditions yielding (1R∗,3S∗)-3-amino-1,4-diols in up to 97% and 70% yield respectively. The major reduction product was converted in two steps to (±)-HPA-12, which is an inhibitor of the cytosolic ceramide transporting protein.en
dc.languageenen
dc.publisherElsevier Ltden
dc.relation.ispartofTetrahedronen
dc.titleA domino Kornblum-DeLaMare/aza-Michael reaction of 3,6-dihydro-1,2-dioxines and application to the synthesis of the ceramide transport inhibitor (±)-HPA-12en
dc.typeJournal Articleen
dc.identifier.doi10.1016/j.tet.2017.11.010en
dc.subject.keywordsBiologically Active Moleculesen
dc.subject.keywordsOrganic Chemical Synthesisen
local.contributor.firstnameSarahen
local.contributor.firstnameMartynen
local.contributor.firstnameJulianen
local.contributor.firstnameChristopher Jen
local.contributor.firstnameBenen
local.subject.for2008030401 Biologically Active Moleculesen
local.subject.for2008030503 Organic Chemical Synthesisen
local.subject.seo2008970103 Expanding Knowledge in the Chemical Sciencesen
local.subject.seo2008860604 Organic Industrial Chemicals (excl. Resins, Rubber and Plastics)en
local.profile.schoolSchool of Rural Medicineen
local.profile.emailslegendr@myune.edu.auen
local.profile.emailjklepp2@myune.edu.auen
local.profile.emailbgreatre@une.edu.auen
local.output.categoryC1en
local.record.placeauen
local.record.institutionUniversity of New Englanden
local.identifier.epublicationsrecordune-20180119-145950en
local.publisher.placeUnited Kingdomen
local.format.startpage1229en
local.format.endpage1239en
local.identifier.scopusid85035117848en
local.peerreviewedYesen
local.identifier.volume74en
local.identifier.issue12en
local.contributor.lastnameLegendreen
local.contributor.lastnameJevricen
local.contributor.lastnameKleppen
local.contributor.lastnameSumbyen
local.contributor.lastnameGreatrexen
dc.identifier.staffune-id:slegendren
dc.identifier.staffune-id:jklepp2en
dc.identifier.staffune-id:bgreatreen
local.profile.orcid0000-0002-0356-4966en
local.profile.roleauthoren
local.profile.roleauthoren
local.profile.roleauthoren
local.profile.roleauthoren
local.profile.roleauthoren
local.identifier.unepublicationidune:22969en
local.identifier.handlehttps://hdl.handle.net/1959.11/22785en
dc.identifier.academiclevelAcademicen
dc.identifier.academiclevelAcademicen
dc.identifier.academiclevelAcademicen
local.title.maintitleA domino Kornblum-DeLaMare/aza-Michael reaction of 3,6-dihydro-1,2-dioxines and application to the synthesis of the ceramide transport inhibitor (±)-HPA-12en
local.output.categorydescriptionC1 Refereed Article in a Scholarly Journalen
local.search.authorLegendre, Sarahen
local.search.authorJevric, Martynen
local.search.authorKlepp, Julianen
local.search.authorSumby, Christopher Jen
local.search.authorGreatrex, Benen
local.uneassociationUnknownen
local.identifier.wosid000427665200010en
local.year.published2018en
local.fileurl.closedpublishedhttps://rune.une.edu.au/web/retrieve/a7ba7322-dcc6-4393-84cb-ee93adb800cben
local.subject.for2020340401 Biologically active moleculesen
local.subject.for2020340503 Organic chemical synthesisen
local.subject.seo2020280105 Expanding knowledge in the chemical sciencesen
local.subject.seo2020240908 Organic industrial chemicals (excl. resins, rubber and plastics)en
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