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Chiral dendralenes for rapid access to enantiomerically pure polycycles

Miller, Natalie; Willis, Anthony; Paddon-Row, Michael; Sherburn, Michael

Description

(Chemical Equation Presented) On a short fuse: Highly stereoselective and atom-efficient domino Diels-Alder/ lactonization/Diels-Alder sequences can be carried out using simple chiral [3]dendralenes to form fused-ring systems. This short and general approach to cross-conjugated systems promotes the rapid assembly of enantiomerically pure polycyclic ring systems common to biologically interesting terpenoids with virtually complete stereocontrol (see scheme).

dc.contributor.authorMiller, Natalie
dc.contributor.authorWillis, Anthony
dc.contributor.authorPaddon-Row, Michael
dc.contributor.authorSherburn, Michael
dc.date.accessioned2015-12-07T22:38:29Z
dc.identifier.issn1433-7851
dc.identifier.urihttp://hdl.handle.net/1885/23470
dc.description.abstract(Chemical Equation Presented) On a short fuse: Highly stereoselective and atom-efficient domino Diels-Alder/ lactonization/Diels-Alder sequences can be carried out using simple chiral [3]dendralenes to form fused-ring systems. This short and general approach to cross-conjugated systems promotes the rapid assembly of enantiomerically pure polycyclic ring systems common to biologically interesting terpenoids with virtually complete stereocontrol (see scheme).
dc.publisherWiley-VCH Verlag GMBH
dc.sourceAngewandte Chemie International Edition
dc.subjectKeywords: Atoms; Polycyclic aromatic hydrocarbons; Self assembly; Stereochemistry; Cross-coupling; Cycloaddition; Dendralenes; Domino reactions; Fused-ring systems; Olefins Cross-coupling; Cycloaddition; Dendralenes; Domino reactions; Fused-ring systems
dc.titleChiral dendralenes for rapid access to enantiomerically pure polycycles
dc.typeJournal article
local.description.notesImported from ARIES
local.identifier.citationvolume46
dc.date.issued2007
local.identifier.absfor030503 - Organic Chemical Synthesis
local.identifier.ariespublicationu4005981xPUB27
local.type.statusPublished Version
local.contributor.affiliationMiller, Natalie, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationWillis, Anthony, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationPaddon-Row, Michael, University of New South Wales
local.contributor.affiliationSherburn, Michael, College of Physical and Mathematical Sciences, ANU
local.description.embargo2037-12-31
local.bibliographicCitation.issue6
local.bibliographicCitation.startpage937
local.bibliographicCitation.lastpage940
local.identifier.doi10.1002/anie.200603335
dc.date.updated2015-12-07T10:38:40Z
local.identifier.scopusID2-s2.0-33846686864
CollectionsANU Research Publications

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