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Dichlorocarbene adducts of alkyl enol ethers as precursors to furans: application to a total synthesis of the furanosesquiterpene (±)-pallescensin A

Foot, Jonathan; Phillis, Andrew; Sharp, Phillip; Willis, Anthony; Banwell, Martin

Description

A novel method for annulating furans to ketones, involving treatment of the dichlorocarbene adduct of the derived methyl enol ether with base, has been exploited in the synthesis of the title natural product 1 from the known trans-decalone 2. Crown

dc.contributor.authorFoot, Jonathan
dc.contributor.authorPhillis, Andrew
dc.contributor.authorSharp, Phillip
dc.contributor.authorWillis, Anthony
dc.contributor.authorBanwell, Martin
dc.date.accessioned2015-12-13T23:03:56Z
dc.identifier.issn0040-4039
dc.identifier.urihttp://hdl.handle.net/1885/85141
dc.description.abstractA novel method for annulating furans to ketones, involving treatment of the dichlorocarbene adduct of the derived methyl enol ether with base, has been exploited in the synthesis of the title natural product 1 from the known trans-decalone 2. Crown
dc.publisherElsevier
dc.sourceTetrahedron Letters
dc.subjectKeywords: carbenoid; decalone; ester derivative; furan derivative; ketone; pallescensin a; sesquiterpene derivative; unclassified drug; annulation reaction; article; chemical reaction kinetics; stereochemistry Cyclopropene; Dichlorocyclopropane; Furan; Furanosesquiterpene; Pallescensin A; Wieland-Miescher ketone
dc.titleDichlorocarbene adducts of alkyl enol ethers as precursors to furans: application to a total synthesis of the furanosesquiterpene (±)-pallescensin A
dc.typeJournal article
local.description.notesImported from ARIES
local.description.refereedYes
local.identifier.citationvolume47
dc.date.issued2006
local.identifier.absfor030503 - Organic Chemical Synthesis
local.identifier.ariespublicationMigratedxPub13383
local.type.statusPublished Version
local.contributor.affiliationFoot, Jonathan, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationPhillis, Andrew, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationSharp, Phillip, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationWillis, Anthony, 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.issue38
local.bibliographicCitation.startpage6817
local.bibliographicCitation.lastpage6820
local.identifier.doi10.1016/j.tetlet.2006.07.068
dc.date.updated2015-12-12T07:52:18Z
local.identifier.scopusID2-s2.0-33747190017
CollectionsANU Research Publications

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