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The Enantiocontrolled Synthesis of a Highly Functionalized Cyclohexenone Related to the A-Ring of the Furanosteroid Viridin

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Findlay, Alison; Gebert, Antje; Cade, Ian; Banwell, Martin

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A seven-step reaction sequence has been used to convert the enantiomerically pure cis-1,2-dihydrocatechol 10 into the cyclohexenone 17a. A near equivalent sequence involving the same starting material has allowed for the synthesis of the regioisomeric system 17b. Compound 17a is related to the A-ring of ent-viridin (ent-1), the non-natural enantiomer of the furanosteroid viridin (1).

dc.contributor.authorFindlay, Alison
dc.contributor.authorGebert, Antje
dc.contributor.authorCade, Ian
dc.contributor.authorBanwell, Martin
dc.date.accessioned2015-12-07T22:14:43Z
dc.identifier.issn0004-9425
dc.identifier.urihttp://hdl.handle.net/1885/17563
dc.description.abstractA seven-step reaction sequence has been used to convert the enantiomerically pure cis-1,2-dihydrocatechol 10 into the cyclohexenone 17a. A near equivalent sequence involving the same starting material has allowed for the synthesis of the regioisomeric system 17b. Compound 17a is related to the A-ring of ent-viridin (ent-1), the non-natural enantiomer of the furanosteroid viridin (1).
dc.publisherCSIRO Publishing
dc.sourceAustralian Journal of Chemistry
dc.subjectKeywords: Functionalized; Reaction sequences; Starting materials
dc.titleThe Enantiocontrolled Synthesis of a Highly Functionalized Cyclohexenone Related to the A-Ring of the Furanosteroid Viridin
dc.typeJournal article
local.description.notesImported from ARIES
local.identifier.citationvolume62
dc.date.issued2009
local.identifier.absfor030503 - Organic Chemical Synthesis
local.identifier.ariespublicationu2544221xPUB2
local.type.statusPublished Version
local.contributor.affiliationFindlay, Alison, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationGebert, Antje, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationCade, Ian, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationBanwell, Martin, College of Physical and Mathematical Sciences, ANU
local.description.embargo2037-12-31
local.bibliographicCitation.issue9
local.bibliographicCitation.startpage1173
local.bibliographicCitation.lastpage1180
local.identifier.doi10.1071/CH09283
dc.date.updated2016-02-24T09:51:25Z
local.identifier.scopusID2-s2.0-70349323009
local.identifier.thomsonID000269853200031
CollectionsANU Research Publications

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